705-62-4

Usage

Type of compound

Thiourea derivative

Structure

Contains a sulfur atom in its molecular structure

Common uses

a. Reagent in organic synthesis
b. Inhibitor in enzyme reactions

Potential properties

a. Antioxidant
b. Anticancer

Physical appearance

White crystalline

Melting point

178-180 degrees Celsius

Solubility

Slightly soluble in water

Applications

Laboratory research and pharmaceutical applications

Upstream product

• 506-77-4 cyanogen chloride 
• 21511-55-7 (methoxymethylidene)dimethylammonium methyl sulfate 
• 103-72-0 phenyl isothiocyanate 
• 4094-46-6 3-Phenyl-4-oxo-2-thioxo-tetrahydro-1,3-thiazin 
• 124-40-3 dimethyl amine 
• 6906-32-7 N,N,2-Trimethyl-1-propen-1-amin 
• 61985-11-3 5-dimethylamino-2-(1,3-dimethyl-thioureido)-4,4-dimethyl-4H-thiazolium betaine 
• 81852-22-4 ethyl cyano<thio>acetate 
• 105936-84-3 1,2-dihydro-2-methoxycarbonylphthalazine-1-carbonitrile 
• 62-53-3 aniline 
• 506-59-2 N,N-dimethylammonium chloride 
• 74734-11-5 1H-imidazole-1-carbodithioic acid methyl ester 
• 16906-70-0 phenyl N,N-dimethyl dithiocarbamate 
• 128-04-1 sodium dimethyldithiocarbamate 

Downstream Products

• 124-40-3 dimethyl amine 
• 102-08-9 N,N-diphenylthiourea 
• 61522-22-3 2-dimethylamino-5-ethoxycarbonyl-4-oxo-3-phenyl-4,5-dihydro-thiazolium betaine 
• 61522-21-2 2-dimethylamino-4-oxo-3,5-diphenyl-4,5-dihydro-thiazolium betaine 
• 20768-83-6 trans-N_.N-Dimethyl-N'-phenyl-N'-(2-methoxycarbonyl-vinyl)-thioharnstoff 
• 96654-31-8 -dithiocarbazinsaeure-methylester 
• 1010-53-3 3-phenyl-2,4-thiazolidinedione 
• 6966-55-8 2-imino-3-phenyl-4-thiazolidinone 
• 86869-44-5 3-phenyl-4-iminothiazolidin-2-one 
• 101-42-8 fenuron 
• 149-30-4 2-thioxo-3H-1,3-benzothiazole 
• 103-72-0 phenyl isothiocyanate 
• 144749-75-7 {Cu(P(C₆H₅)3)2(C₆H₅NHC(S)N(CH₃)2)Br} 
• 144749-76-8 {Cu(P(C₆H₅)3)2(C₆H₅NHC(S)N(CH₃)2)I} 

Relevant academic research and scientific papers

Reaction of N-benzyl azomethine ylide with aryl isothiocyanates: synthesis of (Z)-N-aryl-3-benzylthiazolidine-5-imines

[Figure not available: see fulltext.] The reaction of aryl isothiocyanates with nonstabilized azomethine ylides generated in situ by various methods was studied. It was established that the use of N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine in the presence of trifluoroacetic acid in the role of a catalyst led to the formation of (Z)-N-aryl-3-benzylthiazolidin-5-imines in 22–47% yields.

Aminomethylation of Thioureas with N,N-Dimethyl-1-(triethylsiloxy)methanamine, Involving Amino Group Exchange

The O-triethylsilylated hemiaminal Et3SiOCH2NMe2 readily transfers the Me2NCH2-group to various thioureas under mild conditions and without catalysts or co-reagents. In the reaction with PhNHC(=S)·NHPh, the initially formed mono-substituted derivative PhNHC(=S)NPhCH2NMe2 readily rearranges to produce the unsymmetrical thiourea PhNHC(=S)NMe2 and hexahydro-1,3,5-triphenyl-1,3,5-triazine.

Copper(II)-Promoted Cascade Synthesis of 2-Aminobenzothiazoles Starting from 2-Iodoanilines and Sodium Dithiocarbamates

A facile and efficient formation of 2-aminobenzothiazoles by a copper(II)-promoted one-pot cascade process was developed. The desired 2-aminobenzothiazoles were synthesized in good to excellent yields (up to 97 %) in the presence of Cu(OAc)2 an

Facile synthesis of substituted arylthioureas in the presence of sodium hydride

A series of 11 1,1-dimethyl-3-aryl-thioureas were synthesised in good yields (70-92%) by reacting arylamines with S-aryl-N,Ndimethylthiocarbamate in DMSO in the presence of NaH at 90 °C. It is noteworthy that this method can also be used for arylamines containing a halogen atom at the ortho position.

Hydroamination of carbodiimides, isocyanates, and isothiocyanates by a bis(phosphinoselenoic amide) supported titanium(IV) complex

The hydroamination of heterocumulenes such as carbodiimides, isocyanates, and isothiocyanates by a bis(phosphinoselenoic amide) supported titanium(iv) complex as a precatalyst is reported here. The titanium(iv) complex [{Ph2P(Se)NCH2CH2NPPh2(Se)}Ti(NMe2)2] (1) was synthesised by the reaction of tetrakis-(dimethylamido)titanium(iv) [Ti(NMe2)4] with [{Ph2P(Se)NHCH2CH2NHPPh2(Se)}] in toluene at ambient temperature. Titanium complex 1 proved to be a competent pre-catalyst for the addition of an amine N-H bond to carbodiimides, isocyanates, and isothiocyanates. The reaction scope was expanded to reactions of aliphatic and aromatic amines with phenylisocyanates and phenylisothiocyanates in toluene solvents proceeding rapidly at room temperature with 5 mol% catalyst loadings to yield the corresponding urea and thio-urea derivatives up to 99%. However, ambient temperature was needed for hydroamination of 1,3-dicyclohexylcarbodiimide. The amine addition reactions with isocyanates showed first order kinetics with respect to catalyst 1 as well as substrates. The most plausible mechanism for the hydroamination reaction was established by isolating 1,1-dimethylphenyl urea as a side product.

1-(Methyldithiocarbonyl)imidazole: A useful thiocarbonyl transfer reagent for synthesis of substituted thioureas

1-(Methyldithiocarbonyl)imidazole 1 and its N-methyl quaternary salt 2 have been shown to be efficient methyldithiocarbonyl and thiocarbonyl transfer reagents for the synthesis of dithiocarbamates, symmetrical and unsymmetrical mono-, di- and tri-substituted thioureas in high yields under mild and simple non-hazardous reaction conditions. (C) 2000 Elsevier Science Ltd.

A Concise and Convenient Method for the Synthesis of Pure Substituted Thioureas

Zinc dialkyldithiocarbamates offer excellent substrates for pure thioureas required for the ntifungal and X-ray crystallographic studies.

Cycloaddition Reactions of Heterocumulenes, XXVIII. - A 1,6-Dipole Stabilized by No-Bond Resonance. - Molecular Structure and Reactivity

The X-ray structural investigation of the 1,6-dipole 1 reveals an intramolecular S-N contact of 236 pm, which indicates stabilization by no-bond resonance.In reactions with the heterocumulenes 2-5, the thiazoline ring of 1 is opened to give the heterocycles 7a-f, 8e.The reaction of bis(trimethylsilyl)thioketene (6) takes a deviating pathway: the primary adduct 15 gives a sigmatropic 1,3 shift of the dimethylamino group to yield product 16b.This constitution is derived from an X-ray structural study of the degradation product 17.

Some Reactions of N-Alkoxycarbonyl Reissert Compounds with Heterocumulenes: Formation of the Imidazoisoquinoline and Imidazophthalazine Systems and Related Chemistry

Chloroformate derived Reissert compounds of isoquinoline and of phenanthridine on treatment with base undergo cyclisation with isothiocyanates to give in good yields corresponding imidazoisoquinoline and imidazophenanthroline derivatives.Phthalazine Reissert compound analogues give open chain adducts under the same conditions which can be cyclised to derivatives of the novel imidazophthalazine system by heating in the presence of molecular sieves.When carbon disulphide is the heterocumulene cyclisation is not observed but open chain dithio-ester derivatives can be isolated on alkylation of the intermediate sodium salts.

Cycloaddition Reactions of Heterocumulenes, XXVI. Cycloadducts from Aryl Isothiocyanates and 2,2-Disubstituted Enamines

Aryl isothiocyanates 1 react with enamines 2 to give two types of 2:1 cycloadducts.Below 50 deg C, 1a - g and 2 give rise to 6-imino-1,3-thiazine-2-thiones 5, the constitutions of which are proved by an X-ray analysis of 5c.Above 50 deg C or starting from 4-nitrophenyl isothiocyanate (1h), 2,4-dithiouracils 6 are formed. 1:1 cycloadducts of the reactants are detected spectroscopically; on workup, they hydrolyze to give 2-formylthiopropionanilides 9.