60-56-0

Basic information

• Product Name: Methimazole
• Synonyms: 1,3-dihydro-1-methyl-2h-imidazole-2-thion;1,3-dihydro-1-methyl-2H-Imidazole-2-thione;1-methyl-2-mercapto-imidazol;1-methyl-imidazole-2-thio;1-Metylo 2 merkaptoimidazolem;1-metylo2merkaptoimidazolem;2H-Imidazole-2-thione, 1,3-dihydro-1-methyl-;2H-Imidazole-2-thione,1,3-dihydro-1-methyl-
• CAS NO: 60-56-0
• Molecular Formula: C₄H₆N₂S
• Molecular Weight: 114.17
• EINECS: 200-482-4
• Product Categories: Heterocyclic Compounds;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Bioactive Small Molecules;Building Blocks;Cell Biology;Chemical Synthesis;Heterocyclic Building Blocks;Imidazoles;M;API;TAPAZOLE;Other APIs;Medicine Intermediates;Pharmaceutical intermediates
• Mol File: 60-56-0.mol

Chemical Properties

• Melting Point: 144-147 °C(lit.)
• Boiling Point: 280 °C
• Flash Point: 280°C
• Appearance: White to slightly cream or pale buff/Crystalline Powder
• Density: 1.176 (estimate)
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: Refrigerator
• Solubility: 200g/l
• PKA: 12.37±0.50(Predicted)
• Water Solubility: soluble
• Merck: 14,5971
• BRN: 108646
• CAS DataBase Reference: Methimazole(CAS DataBase Reference)
• NIST Chemistry Reference: Methimazole(60-56-0)
• EPA Substance Registry System: Methimazole(60-56-0)

Safety Data

• Hazard Codes: Xn
• Statements: 43-62-63-22
• Safety Statements: 26-27-36-45-36/37
• WGK Germany: 3
• RTECS: NI8615000
• TSCA: Yes
• Hazardous Substances Data: 60-56-0(Hazardous Substances Data)

Usage

description

Methimazole is an antithyroid medication used in the therapy of hyperthyroidism and Graves disease. It works by making it harder for the body to make thyroid hormone. It is also known as thiamazole, is a thioamide and a thyroid hormone antagonist which acts by inhibiting the incorporation of iodine into tyrosyl residues of thyroglobulin and, thus, lowering thyroid hormone levels. It resembles propylthiouracil both in chemical structure and activity. Methimazole is primarily used for the treatment of hyperthyroidism, by inhibiting the peroxidase system, hindering thyroxine (T4) and tri-triiodothyronine (T3) synthesis, animal experiments show that it can inhibit B lymphocytes synthesizing antibodies, and reduce levels of thyroid stimulating antibodies in blood circulating it can make suppressing T cell function return to normal, it is applicable to hyperthyroidism caused by a variety of factors . Like other various drugs (propylthiouracil), it also has some adverse reactions while it is taken, Including hematologic adverse reactions, primarily neutropenia, hematopoietic dysfunction or disorder, thrombocytopenia, reduction of prothrombin or factor VII ; long-term medication can also cause liver damage,such as cholestatic jaundice and toxic hepatitis ; other skin reactions such as hair loss, itching, rash, dermatitis, lupus erythematosus, as well as some other rare adverse reactions. Also methimazole allows prothrombin time to prolong , and increases serum alkaline phosphatase, aspartate aminotransferase (AST) and alanine aminotransferase (ALT)and causes blood bilirubin and blood lactate dehydrogenase increasing. Therefore, patients in the medication should regularly take blood tests, liver function tests and peripheral blood leukocytes. The above information is edited by the lookchem of Tian Ye.

Chemical properties

leaf-shaped crystalline (ethanol), melting point 146-148 ℃, boiling point 280 ℃ (decomposition), soluble in water, soluble in alcohol, chloroform, slightly soluble in ether, benzene.

Uses

Different sources of media describe the Uses of 60-56-0 differently. You can refer to the following data:
1. Carbimazole intermediates. anti-thyroid drugs.
2. Methimazole also directly disrupts thyroxine and triiodothyronin sysnthesis in the thyroid gland, and it is used for the same indications as propylthiouracil and methylthiouracil to treat hyperfunctioning thyroid glands in patients with Basedow’s disease.
3. Methimazole is a thiourea antithyroid agent that prevents iodine organification, thus inhibiting the synthesis of thyroxine. Antihyperthyroid
4. 2-Mercapto-1-methylimidazole was employed as hydrophobic charge-induction chromatography ligand for antibody purification. It was also used in preparation of nitrile functionalized methimazole-based room temperature ionic liquids.

Production methods

React amino acetal with methyl isothiocyanate to genarate this product. The product can also be produced from thiocyanate and N-substituted amino acetal.

Chemical Properties

White Solid

Originator

Favistan ,Asta

Manufacturing Process

2 Methods of preparation of thiamazole: 1. To 2,2-diethoxyethylamine methylisothiocyanate was added and mixed after then 1-(2,2-diethoxy-ethyl)-3-methylthiourea was obtained. The reaction of the 1-(2,2-diethoxyethyl)-3-methylthiourea with sulfuric acid yield thiamazole. 2. 1,1-Diethoxyethane was treated by bromine in the presence CaCO3 and 2- bromo-1,1-diethoxyethane was obtained. Then to the 2-bromo-1,1-diethoxyethane methylamine was added, mixed and reaction mixture was heated to 120°-130°C in autoclave. As the result (2,2- diethoxyethyl)methylamine was obtained. (2,2-Diethoxyethyl)methylamine reacted with potassium thiocyanate in the presence of hydrochloric acid and give the thiamazole, yellow crystallic precipitate, melting point 144°-147°C.

Brand name

Tapazole (Jones); Tapazole (King) .

General Description

Methimazole, 1-methylimidazole-2-thiol (Tapazole), occurs as a white to off-white, crystallinepowder with a characteristic odor and is freely soluble inwater. A 2% aqueous solution has a pH of 6.7 to 6.9. It shouldbe packaged in well-closed, light-resistant containers.

Biochem/physiol Actions

Methimazole is a thiourea antithyroid agent that prevents iodine organification, thus inhibiting the synthesis of thyroxine.

Clinical Use

Methimazole is indicated in the treatment of hyperthyroidism.It is more potent than propylthiouracil. The side effectsare similar to those of propylthiouracil. As with otherantithyroid drugs, patients using this drug should be undermedical supervision. Also, like the other antithyroid drugs,methimazole is most effective if the total daily dose is subdividedand given at 8-hour intervals.

Safety Profile

Poison by subcutaneous route. Moderately toxic by ingestion and intraperitoneal routes. Human teratogenic effects. An experimental teratogen. Experimental reproductive effects. Questionable carcinogen with experimental neoplastigenic data. Human mutation data reported. An antithyroid drug. When heated to decomposition it emits very toxic fumes of NOx and SOx. See also MERCAPTANS.

Synthesis

Methimazole, 1-methyl-2-imidazolthiol (25.2.5), is synthesized by reacting aminoacetic aldehyde diethylacetal with methylisothiocyanate and subsequent hydrolysis of the acetal group of the resulting disubstituted urea derivative 25.2.4 by a solution of sulfuric acid, during which a simultaneous cyclization reaction takes place, forming the imidazole ring of the desired methimazole .

Veterinary Drugs and Treatments

Methimazole is considered by most clinicians to be the agent of choice when using drugs to treat feline hyperthyroidism. Propylthiouracil has significantly higher incidences of adverse reactions when compared to methimazole and is rarely used today. Transdermal methimazole (in PLO gel; 2.5 mg twice daily) has been used with some therapeutic success in cats that do not tolerate oral dosing. Efficacy may require four or more weeks to detect. Studies are ongoing. Methimazole appears to be useful for the prophylactic prevention of cisplatin induced nephrotoxicity in dogs.

Purification Methods

Crystallise it from EtOH. UV: at 251nm (H2O), 260nm (EtOH) and 267nm (CHCl3). [Lawson max & Morley J Chem Soc 1103 1956, Beilstein 24 H 17, 24 III/IV 61.]

InChI:InChI=1/C4H6N2S/c1-6-3-2-5-4(6)7/h2-3H,1H3,(H,5,7)

Synthetic route

2-tert-butylthio-1-methyl-1H-imidazole (79487-94-8) → 2-Mercapto-1-methylimidazole (60-56-0)

Conditions	Yield
With aluminum (III) chloride at 20℃; Reagent/catalyst; Inert atmosphere;	91%

1-methyl-1H-imidazole (616-47-7) → 2-Mercapto-1-methylimidazole (60-56-0)

Conditions	Yield
Stage #1: 1-methyl-1H-imidazole With n-butyllithium In tetrahydrofuran; hexane at -10℃; for 1.5h; Stage #2: With sulfur In tetrahydrofuran; hexane for 9h; Temperature; Reflux;	82.54%

S-2-(1-methyl)imidazolyl ethanethioate → 2-Mercapto-1-methylimidazole (60-56-0)

Conditions	Yield
With hydrogenchloride In isopropyl alcohol at 20℃; for 5h; Solvent;	77%

2-(benzylthio)-1-methyl-1H-imidazole (63348-55-0) → 3-methyl-1-benzyl-1,3-dihydroimidazole-2-thione (23269-08-1) + 2-Mercapto-1-methylimidazole (60-56-0)

Conditions	Yield
In methanol for 5h; Irradiation;	A 168 mg B 88 mg

hydrogenchloride (7647-01-0) + potassium thioacyanate (333-20-0) + N-methylaminoacetaldehyde diethyl acetal (20677-73-0) → 2-Mercapto-1-methylimidazole (60-56-0)

N-(2,2-diethoxy-ethyl)-N'-methyl-thiourea (90203-43-3) + H2SO4 (diluted ) → 2-Mercapto-1-methylimidazole (60-56-0)

isothiocyanic acid (3129-90-6) + N-methylaminoacetaldehyde diethyl acetal (20677-73-0) → 2-Mercapto-1-methylimidazole (60-56-0)

2,2'-dithiodi(1-methylimidazole) bis(perchloric acid) salt → 1-methyl-1H-imidazole (616-47-7) + 2-Mercapto-1-methylimidazole (60-56-0)

Conditions	Yield
With Carbonate buffer at 25℃; Kinetics;

potassium thioacyanate (333-20-0) + N-methylaminoacetaldehyde diethyl acetal (20677-73-0) → 2-Mercapto-1-methylimidazole (60-56-0)

Conditions	Yield
With hydrogenchloride In water at 20 - 30℃; Large scale;	150 kg

sodium thiocyanide (540-72-7) + N-(methyl)aminoacetaldehyde dimethyl acetal (122-07-6) → 2-Mercapto-1-methylimidazole (60-56-0)

Conditions	Yield
With hydrogenchloride In water at 20 - 60℃; pH=1 - 2;	0.86 kg

6-chloro-pyridine-2-carbonitrile (33252-29-8) + 2-Mercapto-1-methylimidazole (60-56-0) → 2-Cyano-6-(1-methyl-1H-imidazol-2-yl)thiopyridine

Conditions	Yield
With sodium hydride In DMF (N,N-dimethyl-formamide) at 70℃; for 18h;	100%

1-bromo-3-(4-chloro-phenyl)-3-methyl-butan-2-one (99519-64-9) + 2-Mercapto-1-methylimidazole (60-56-0) → 3-(4-chloro-phenyl)-3-methyl-1-(1-methyl-1H-imidazol-2-ylsulfanyl)-butan-2-one (1185752-50-4)

Conditions	Yield
With triethylamine In acetonitrile at 20℃;	100%

1-iodo-(Z)-11-eicosene (72434-98-1) + 2-Mercapto-1-methylimidazole (60-56-0) → C24H44N2S*HI

Conditions	Yield
In acetonitrile at 40 - 45℃; for 72h; Darkness; Inert atmosphere;	100%

(Z)-16-iodohexadec-7-ene + 2-Mercapto-1-methylimidazole (60-56-0) → C20H36N2S*HI

Conditions	Yield
In acetonitrile at 40 - 45℃; for 72h; Darkness; Inert atmosphere;	100%

oleyl iodide (73120-38-4, 69674-78-8) + 2-Mercapto-1-methylimidazole (60-56-0) → HI*C22H40N2S

Conditions	Yield
In acetonitrile at 40 - 45℃; for 72h; Darkness;	100%

(E)-1-iodo-1-octene (42599-17-7) + 2-Mercapto-1-methylimidazole (60-56-0) → (E)-1-methyl-2-(oct-1-enylthio)-1H-imidazole

Conditions	Yield
With potassium phosphate; (1,10-phenanthroline)bis(triphenylphosphine)copper(I) nitrate In toluene at 110℃; for 24h;	99%

(trimethylphosphine)gold(I) chloride (15278-97-4) + 2-Mercapto-1-methylimidazole (60-56-0) → (C3H3N2(CH3)S)(trimethylphosphine gold(I)) (1355252-24-2)

Conditions	Yield
With NaOH In methanol to thiol-compd. in CH3OH NaOH added, stirred for 5 min at room temp., Au-compd. added, stirred for 1 h; evaporated in vac., elem. anal.;	99%

(triethylphosphine)chlorogold(I) (15529-90-5) + 2-Mercapto-1-methylimidazole (60-56-0) → (C3H3N2(CH3)S)(triethylphosphine gold(I)) (1355252-25-3)

Conditions	Yield
With NaOH In methanol to thiol-compd. in CH3OH NaOH added, stirred for 5 min at room temp., Au-compd. added, stirred for 1 h; evaporated in vac., elem. anal.;	99%

(triphenylphosphine)gold(I) chloride (14243-64-2) + 2-Mercapto-1-methylimidazole (60-56-0) → (C3H3N2(CH3)S)(triphenylphosphine gold(I)) (1355252-26-4)

Conditions	Yield
With NaOH In methanol to thiol-compd. in CH3OH NaOH added, stirred for 5 min at room temp., Au-compd. added, stirred for 1 h; evaporated in vac., elem. anal.;	99%

N-(2,4-dimethylphenyl)-2,2,2-trifluoroethanimidoyl chloride (70314-82-8) + 2-Mercapto-1-methylimidazole (60-56-0) → 1-(1-((2,4-dimethylphenyl)imino)-2,2,2-trifluoroethyl)-3-methyl-1H-imidazole-2(3H)-thione

Conditions	Yield
Stage #1: 2-Mercapto-1-methylimidazole With sodium hydride In acetonitrile at 25℃; for 0.5h; Stage #2: N-(2,4-dimethylphenyl)-2,2,2-trifluoroethanimidoyl chloride In acetonitrile at 25℃; for 9h;	99%

2,2,2-trifluoro-N-(3-(trifluoromethyl)phenyl)acetimidoyl chloride (69563-07-1) + 2-Mercapto-1-methylimidazole (60-56-0) → 1-methyl-3-(2,2,2-trifluoro-1-((3-(trifluoromethyl)phenyl)imino)ethyl)-1H-imidazole-2(3H)-thione

Conditions	Yield
Stage #1: 2-Mercapto-1-methylimidazole With sodium hydride In acetonitrile at 25℃; for 0.5h; Stage #2: 2,2,2-trifluoro-N-(3-(trifluoromethyl)phenyl)acetimidoyl chloride In acetonitrile at 25℃; for 9h;	99%

dimethyl acetylenedicarboxylate (762-42-5) + triphenylphosphine (603-35-0) + 2-Mercapto-1-methylimidazole (60-56-0) → dimethyl 2-[(1-methyl-1H-imidazol-2-yl)sulfanyl]-3-(1,1,1-triphenyl-λ5-phosphanylidene)succinate

Conditions	Yield
In ethyl acetate at 20℃; for 5h;	98%

Diisopropyl acetylenedicarboxylate (14447-03-1) + triphenylphosphine (603-35-0) + 2-Mercapto-1-methylimidazole (60-56-0) → diisopropyl 2-[(1-methyl-1H-imidazol-2-yl)sulfanyl]-3-(1,1,1-triphenyl-λ5-phosphanylidene)succinate

Conditions	Yield
In ethyl acetate at 20℃; for 5h;	98%

1,4-diphenyl-but-2-yne-1,4-dione (1087-09-8) + 2-Mercapto-1-methylimidazole (60-56-0) → 2-[(1-methyl-1H-imidazol-2-yl)sulfanyl]-1,4-diphenylbutane-1,4-dione

Conditions	Yield
With triphenylphosphine	98%

4,5-difluoro-2-nitroaniline (78056-39-0) + 2-Mercapto-1-methylimidazole (60-56-0) → 5-(1-methyl-1H-imidazol-2-ylthio)-4-fluoro-2-nitrobenzenamine (849236-50-6)

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 60℃; for 5h;	98%

silver perchlorate monohydrate (14242-05-8) + (bis(diphenylphosphino)methane)bis(chlorogold(I)) (37095-27-5) + 2-Mercapto-1-methylimidazole (60-56-0) → [Au2(μ-bis(diphenylphosphino)methane)(2-mercapto-1-methylimidazole)](ClO4)2

Conditions	Yield
In tetrahydrofuran byproducts: AgCl; N2-atmosphere, in dark; addn. of 2 equiv. AgClO4 to Au-complex, standingfor 0.5 h, filtration, addn. of stoich. amt. mercaptoimidazole, standin g for 0.5 h (pptn.); collection (centrifugation); second crop from mother liquor; elem. anal.;	98%

bismuth(III) chloride + acetone (67-64-1) + 2-Mercapto-1-methylimidazole (60-56-0) → C16H24Bi2Cl6N8S4*C3H6O

Conditions	Yield
In methanol for 3h;	98%

Di-tert-butyl acetylenedicarboxylate (66086-33-7) + triphenylphosphine (603-35-0) + 2-Mercapto-1-methylimidazole (60-56-0) → di-tert-butyl 2-[(1-methyl-1H-imidazol-2-yl)sulfanyl]-3-(1,1,1-triphenyl-λ5-phosphanylidene)succinate

Conditions	Yield
In ethyl acetate at 20℃; for 5h;	97%

sodium tetrahydroborate (16940-66-2) + thallium(I) acetate (563-68-8) + 2-Mercapto-1-methylimidazole (60-56-0) → thallium(I) bis(2-mercapto-1-methylimidazolyl)borate

Conditions	Yield
In tetrahydrofuran; methanol; water byproducts: CH3COONa; suspn. of NaBH4 and S compd. in THF refluxed for 15 h under Ar, cooled to room temp., solvent removed in vac., solid dissolved in MeOH, aq. soln. of TlOAc added, stirred for 15 min; filtered, washed with water, dried in vac. for 2.5 h; elem. anal.;	97%

2-bromo-1-(2,4,6-trimethylphenyl)ethanone (4225-92-7) + 2-Mercapto-1-methylimidazole (60-56-0) → 2-(1-methyl-1H-imidazol-2-ylsulfanyl)-1-(2,4,6-trimethyl-phenyl)-ethanone (1154952-09-6)

Conditions	Yield
With triethylamine In acetonitrile at 20℃;	97%

2-bromo-1-[1-(4-chloro-phenyl)-cyclopropyl]-ethanone (1185023-08-8) + 2-Mercapto-1-methylimidazole (60-56-0) → 1-[1-(4-chloro-phenyl)-cyclopropyl]-2-(1-methyl-1H-imidazol-2-ylsulfanyl)-ethanone (1185751-91-0)

Conditions	Yield
With triethylamine In acetonitrile at 20℃;	97%

1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane (2043-57-4) + 2-Mercapto-1-methylimidazole (60-56-0) → C12H9F13N2S*HI

Conditions	Yield
In ethanol for 36h; Reflux;	97%

2-fluoro-5-phenyl-3-trifluoromethylthiophene (155262-17-2) + 2-Mercapto-1-methylimidazole (60-56-0) → 2-(1-methylimidazol-2-ylmercapto)-5-phenyl-3-trifluoromethylthiophene

Conditions	Yield
With potassium hydroxide In 1,4-dioxane Heating;	96%

triphenylphosphine (603-35-0) + 2-Mercapto-1-methylimidazole (60-56-0) + acetylenedicarboxylic acid diethyl ester (762-21-0) → diethyl 2-[(1-methyl-1H-imidazol-2-yl)sulfanyl]-3-(1,1,1-triphenyl-λ5-phosphanylidene)succinate

Conditions	Yield
In ethyl acetate at 20℃; for 5h;	96%

7-methoxy-2-methylsulfonyl-3-phenyl-4H-1-benzopyran-4-one (658040-87-0) + 2-Mercapto-1-methylimidazole (60-56-0) → 7-methoxy-2-(1-methyl-1H-imidazol-2-ylsulfanyl)-3-phenyl-chromen-4-one

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h;	96%

ethyl-2-bromooctanoate (138286-76-7, 5445-29-4) + 2-Mercapto-1-methylimidazole (60-56-0) → 2-(1-methyl-1H-imidazol-2-yl-sulfanyl)-octanoic acid ethyl ester (212769-61-4)

Conditions	Yield
	96%
	96%

2-Mercapto-1-methylimidazole (60-56-0) → 1-methyl-1H-imidazole-2-sulfonic acid (137048-30-7)

Conditions	Yield
With chlorine dioxide In water for 0.5h;	96%

E-styryl iodide (42599-24-6) + 2-Mercapto-1-methylimidazole (60-56-0) → (E)-1-methyl-2-(styrylthio)-1H-imidazole

Conditions	Yield
Stage #1: 2-Mercapto-1-methylimidazole With potassium fluoride; copper(l) iodide; cis-1,2-cyclohexane In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: E-styryl iodide In N,N-dimethyl-formamide at 90℃; for 12h;	96%

dichloromethane (75-09-2) + 2-Mercapto-1-methylimidazole (60-56-0) → 1,1'-methylenebis(1,3-dihydro-3-methyl-1H-imidazole-2-thione) (133213-39-5)

Conditions	Yield
In tetrahydrofuran; methanol at 80℃; for 26h; Sealed tube;	95.8%
at 79.84℃; for 24h;	89%

2-Mercapto-1-methylimidazole (60-56-0) + 2-Chloromethyl-4-(3,4-dimethoxy-phenyl)-quinoline-3-carboxylic acid ethyl ester → 4-(3,4-Dimethoxy-phenyl)-2-(1-methyl-1H-imidazol-2-ylsulfanylmethyl)-quinoline-3-carboxylic acid ethyl ester

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 3h; Ambient temperature;	95%

Upstream product

• 7647-01-0 hydrogenchloride 
• 333-20-0 potassium thioacyanate 
• 20677-73-0 N-methylaminoacetaldehyde diethyl acetal 
• 79487-94-8 2-tert-butylthio-1-methyl-1H-imidazole 
• 540-72-7 sodium thiocyanide 
• 122-07-6 N-(methyl)aminoacetaldehyde dimethyl acetal 
• 616-47-7 1-methyl-1H-imidazole 
• 3129-90-6 isothiocyanic acid 
• 90203-43-3 N-(2,2-diethoxy-ethyl)-N'-methyl-thiourea 
• 63348-55-0 benzyl N-methyl-2-imidazolyl sulfide 
• 39799-77-4 1-methyl-1,3-dihydro-2H-imidazol-2-one 
• 73395-65-0 anhydro-2-Hydroxy-8-methyl-4-oxo-3-phenyl-4H-imidazo<2,1-b><1,3>thiazinium hydroxide 
• 100-46-9 benzylamine 
• 61747-29-3 bis(1-methyl-1H-imidazole-2-yl)disulfide 

Downstream Products

• 242486-25-5 (triphenylphosphine)(1-methyl-imidazoline-2(3H)-thione)2(nitrate)-copper(I) 
• 96591-89-8 6-(1-Methyl-1H-imidazol-2-ylsulfanyl)-pyridine-3-sulfonic acid amide 
• 39259-57-9 2-(1-methyl-1H-imidazol-2-ylsulfanyl)-5-nitro-thiazole 
• 87008-53-5 2-(2,4-Dinitro-phenylsulfanyl)-1-methyl-1H-imidazole; hydrochloride 
• 131470-53-6 (2-Mercapto-3-methyl-3H-imidazol-4-yl)-m-tolyl-methanol 
• 327188-53-4 4-(4-chlorophenyl)-5-[3-(2-methoxyphenoxy)propyl]-2-(1-methyl-2-imidazolylsulfanyl)oxazole 
• 14486-52-3 2-methylmercapto-3-methylimidazole 
• 133303-83-0 2[[4-(Trifluoromethyl)phenyl]thio]-1-methyl-1H-imidazole hydrochloride 
• 131470-63-8 2-Mercapto-1-methyl-5-(phenylthio)imidazole 
• 131470-56-9 Biphenyl-4-yl-(2-mercapto-3-methyl-3H-imidazol-4-yl)-methanol 
• 131470-54-7 (2-Mercapto-3-methyl-3H-imidazol-4-yl)-o-tolyl-methanol 
• 78843-88-6 1-benzyl-S-(2-N-methyl imidazolyl)-isothiouronium dihydrochloride 
• 63348-55-0 benzyl N-methyl-2-imidazolyl sulfide 
• 131470-62-7 (2-Mercapto-3-methyl-3H-imidazol-4-yl)-phenyl-methanol 

Relevant articles and documents

new synthetic process for thiamazole

The present invention relates to a novel synthesis method capable of synthesizing thiamazole by simple heat treatment of methylimidazole and S_8. The present invention provides a safe and low-cost method for synthesizing thiamazole.

Preparation method of 2 -mercapto -1 - methylimidazole

The invention discloses a preparation method of electronic grade 2-sulfydryl-1-methylimidazole. The method comprises the following steps: (1) a water solution of chloroacetaldehyde dimethyl acetal andmethylamine performs tank closing reaction for 16h at 80 to 85 DEG C; cooling and pressure release are performed; a solvent is used for extraction; the solvent is concentrated; rectification under vacuum is performed to obtain an intermediate of methylaminoacetaldehyde dimethyl acetal; (2) the methylaminoacetaldehyde dimethyl acetal and t-butyl thionitrile react under the boron trifluoride catalysis; condensation reaction is performed at 50 to 70 DEG C to obtain 2-tert-butyl sulfenyl-1-methylimidazole; (3) a solvent is added into the 2-tert-butyl sulfenyl-1-methylimidazole; a catalyst and anorganic solvent are added; reaction is performed at constant temperature; after filtering, filter liquid is concentrated; then, electronic grade water crystallization is performed to obtain the product of 2-sulfydryl-1-methylimidazole. The preparation method has the advantages that the raw material price is low; the environment-friendly effect is achieved; the operation of the synthesis method issimple and convenient; the product quality conforms to application standards of electronic chemicals.

Oxidant/complexing properties of the methimazole (MeImHS)/iodine system towards palladium and gold metals. Crystal structure of the complex cation [PdII(MeImHS)4]2+ balanced by a tetraiodide/iodide mixture

This paper reports on the oxidative dissolution ability in dichloromethane and water of the methimazole-iodine system towards gold and palladium in powder. This research has a potential application in the recovery process of these metals from electrical and electronic waste equipment (WEEE). The iodine-adduct of methimazole (1-methyl-3H-imidazole-2-thione; MeImHS) oxidises gold and palladium powders in dichloromethane to form the complexes [AuI(MeImHS)2]I3 and [PdII(MeImHS)4](I4)0.73·2(I)0.27. The X-ray crystal structure of the palladium complex shows a square-planar Pd(ii) ion S-coordinated to four MeImHS units with the charge essentially balanced by an unusual tetraiodide I42- with minor amounts of iodide. The oxidative dissolution of palladium in water medium produces the cation [PdII(MeImHS)4]2+. Considering the reaction conditions under which the process was performed ([I2] = 1.14 × 10-3 M, T = 20 °C, pH = 5, reaction time 24 h), the obtained value of 64% of oxidation yields from Pd(0) to Pd(ii) is to be considered satisfactory. No appreciable oxidation was observed for the gold powder in water. The feasibility of recovering palladium from the triiodide salt of the complex cation [PdII(MeImHS)4]2+ was verified by carrying out a two-step reduction process using magnesium powder.

Methimazole preparation method

The invention discloses a methimazole preparation method, which comprises: 1) carrying out an ammonolysis reaction on dimethylchloroacetal and a methylamine methanol solution at a temperature of 125-135 DEG C, adding the alkoxide of an alkali metal after completing the reaction, carrying out a neutralization reaction, filtering, distilling to remove the methanol, and carrying out pressure reducing distillation to obtain an intermediate methylamino dimethoxyethane; and 2) adding sodium thiocyanate and the methylamino dimethoxyethane obtained in the step 1) into purified water, adding hydrochloric acid at a room temperature in a dropwise manner, carrying out a reaction for 12-15 h at a temperature of 50-60 DEG C, carrying out pressure reducing distillation to remove the water after completing the reaction, adding ethyl acetate and a drying agent, carrying out heating reflux for 30 min, carrying out hot filtering, distilling the filtrate until the remaining volume of the ethyl acetate is 1/3, and carrying out cooling crystallization to obtain the methimazole. According to the present invention, the preparation method has advantages of low cost, short route, convenient operation and environmental protection, and the high-quality methimazole can be obtained through the method.

Methimazole synthesizing and purifying method

The invention discloses a methimazole synthesizing and purifying method, and belongs to the field of medicine synthesis. The method comprises the following steps: carrying out a condensation reaction on methylaminoacetaldehyde polyethylene glycol and ammonium thiocyanate which are used as raw materials in the presence of an acid catalyst and a phase transfer catalyst; and adding saturated salt water after the reaction is completed, uniformly mixing the obtained reaction product and the saturated salt water, adding an organic solvent to carry out extraction, drying and concentrating the obtained organic layer to obtain crude methimazole, heating and dissolving the crude product in a solvent, adding active carbon to decolorize the obtained solution, filtering the solution, and drying the filtered solution to obtain purified methimazole. The method is a preparation method simple to operate and suitable for industrial production.

A 2 - mercapto - 1 - alkyl imidazole of preparation method (by machine translation)

The invention discloses a 2 - mercapto - 1 - alkyl imidazole synthesis method, which belongs to the technical field of organic synthesis. Imidazole and alkyl halide in the presence of an inorganic base sealing reaction the temperature of the 1 - alkyl imidazole, then dissolved in ether in the solvent, the low temperature by adding 1 - 1.1 equivalent BuLi, then adding 0.9 - 0.95 equivalent powder reflux reaction, after cooling add acetyl chloride to obtain 2 - acetyl thio - 1 - alkyl imidazole; the final 2 - acetyl thio - 1 - alkyl imidazole dissolved in alcohol solvent, adding a catalytic amount of hydrogen chloride or potassium carbonate deprotection, to obtain 2 - mercapto - 1 - alkyl imidazole. The raw material of the invention is cheap, and more friendly to the environment, the advantages of easy operation, the quality of the product in accordance with the electronic chemicals using standard. (by machine translation)

Methimazole preparation process

The invention provides a methimazole preparation process including the following steps: 1) with 1-methyl-1,3-2H-imidazole-2-one as a raw material and with cooperation of a reaction solvent, vulcanizing the raw material through a vulcanization reagent to obtain a methimazole crude product; and 2) recrystallizing the crude product obtained in the step 1) to obtain the finished product. With 1-methyl-1,3-2H-imidazole-2-one as the raw material, the common vulcanization reagent is used for vulcanization, and methimazole with light color, high purity and low content of metal ions is obtained; and the whole preparation process is simple, has the advantages of easy operation and lower cost, and is suitable for industrial promotion and application.

Preparation method of methimazole

The invention relates to a preparation method of methimazole. The method specifically comprises the following step: enabling reaction of N-methylimidazole, N-butyllithium and powdered sulfur in an organic solvent to obtain methimazole. The preparation method disclosed by the invention is simple in process, mild in condition, simple to operate, easy for post treatment, applicable for industrialized production, and capable of greatly improving the reaction yield of methimazole.

2-mercapto-1-methyl imidazole industrial production method

The invention relates to an industrialization production method of antithyroid drug 2-mercapto-1-methylimidazole. The method comprises: (a) reacting vinyl acetate with bromine in absolute ethyl alcohol, regulating a pH value into alkalescence after reaction, obtaining a bromoacetaldehyde diethyl acetal crude product after extraction and desolventization, and directly adding the bromoacetaldehyde diethyl acetal crude product into a next step of reaction; (b) performing aminolysis reaction of bromoacetaldehyde diethyl acetal and methylamine aqueous solution, and after completing reaction, obtaining methylamino acetal through distilling, separating and purifying after extraction and de-watering; (3) dropping hydrochloric acid into aqueous solution of methylamino acetal and potassium rhodanide; removing water in the reaction solution by reduced pressure distillation after reaction, removing a part insoluble in ethyl acetate from the obtained solid, dissolving residual solid into water with pH being 1-2, crystallizing to obtain 2-mercapto-1-methylimidazole with purity higher than 99%, and then vacuum-drying to obtain a finished product. The production method has a short product line, can obtain 2-mercapto-1-methylimidazole with high purity, and has a strong industrialization prospect.

Synthesis and crystal structures of new 1,3-disubstituted imidazoline-2-thiones

Two methods (MeOH=K2CO3, pyridine=Et3N) were assessed for the introduction of sulfur into the 2-position of 1,3-disubstituted quaternary imidazolium salts 1-9 (Cl, I, BF4, PF6, CH3OSO3 were used as anions) to yield nine 1,3-disubstituted imidazoline-2-thiones 10-18 (1, 10: R1 = CH 3, R2 = CH3; 2, 11: R1 = OCH 2Ph, R2 = CH3; 3, 12: R1 = OCH 3, R2 = CH3; 4, 13: R1 = OCH 3, R2 = OCH3; 5, 14: R1 = NH 2, R2 = CH2Ph; 6, 15: R1 = NCHPh, R2 = CH3; 7, 16: R1 = NH2, R 2 = CH3; 8, 17: R1 = NCHPh, R2 = NCHPh; 9, 18: R1 = NH2, R2 = OCH3). Compounds 11-18 represent N-alkyloxy and N-amino imidazoline-2-thiones, whereas 10 served as reference compound. The first method was advantageous for the conversion 1 → 10 due to faster reaction, whereas in the reaction 2 → 11 considerable amounts of by-products were formed. Pure thiones 11, 14, 16, 17, and 18 were obtained only by the second method. Both methods worked for the synthesis of the methoxy derivatives 12 and 13 from 3 and 4, and the benzylideneamino derivative 15 from 6. 1-Amino-3- methylimidazoline-2-thione (16) was also prepared by hydrolysis of the benzylideneamino derivative 15. Crystal structures of seven 1,3-disubstituted imidazoline-2-thiones were determined by singlecrystal X-ray diffraction. Intermolecular C-H...S contacts were identified and, additionally, N-H...S interactions in aminothiones 14 and 16. The 1H NMR shifts of 10 and 13 were satisfactorily correlated with the Kamlet-Abboud-Taft π* and β parameters in ten solvents. From the lack of correlation with the a parameter and from the C=S bond length (average 1.68 A ) a significant contribution of a mesoionic imidazolium-2-thiolate resonance structure seems unlikely.