10191-60-3

Basic information

• Product Name: N-Cyanoimido-S,S-dimethyl-dithiocarbonate
• Synonyms: s,s-dimethyl cyanoimidodithiocarbonate;S,S'-DIMETHYL N-CYANODITHIOIMINOCARBONATE;N-CYANO-S,S'-DIMETHYLDITHIOIMIDOCARBONATE;N-CYANO-S,S-DIMETHYLDITHIOIMIDOCARBONATE;N-CYANOIMIDO-S,S-DIMETHYL-DITHIOCARBONATE;(Cyanoimino)bis(methylthio)methane;Carbonimidodithioic acid, cyano-, dimethyl ester;Carbonimidodithioicacid,cyano-,dimethylester
• CAS NO: 10191-60-3
• Molecular Formula: C₄H₆N₂S₂
• Molecular Weight: 146.23
• EINECS: 233-467-6
• Product Categories: Pharmaceutical Intermediates;Organic Building Blocks;Others;Sulfur Compounds;organic chemical;Pharmaceutical Intermediate
• Mol File: 10191-60-3.mol
• Article Data: 18

Chemical Properties

• Melting Point: 45-50 °C(lit.)
• Boiling Point: 229.6 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: /solid
• Density: 1.298 (estimate)
• Vapor Pressure: 0.0691mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Slightly soluble in methanol.
• PKA: -5.10±0.50(Predicted)
• BRN: 635998
• CAS DataBase Reference: N-Cyanoimido-S,S-dimethyl-dithiocarbonate(CAS DataBase Reference)
• NIST Chemistry Reference: N-Cyanoimido-S,S-dimethyl-dithiocarbonate(10191-60-3)
• EPA Substance Registry System: N-Cyanoimido-S,S-dimethyl-dithiocarbonate(10191-60-3)

Safety Data

• Hazard Codes: C,T
• Statements: 22-34-23/24/25-36/37
• Safety Statements: 26-36/37/39-45-38-28A-7/9
• RIDADR: UN 1759 8/PG 2
• WGK Germany: 3
• F: 13-19
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 10191-60-3(Hazardous Substances Data)

Usage

Chemical Properties

yellow crystalline powder

Uses

Dimethyl cyanodithioiminocarbonate has been used in the synthesis of 4-methylthiopyrazolo[1,5-a]-1,3,5-triazines, methylsulfanylpyrimidines, cyanoguanidines and N-aryl-6-methylsulfanyl-4-oxopyrimidine-5-carbonitriles. It has been also used in the synthesis of methylsulfanyl derivatives of azoloazines and azoloazoles.

InChI:InChI=1/C4H6N2S2/c1-7-4(8-2)6-3-5/h1-2H3

Synthetic route

carbon disulfide (75-15-0) + CYANAMID (420-04-2) + dimethyl sulfate (77-78-1) → dimethyl N-cyanodithioiminocarbonate (10191-60-3)

Conditions	Yield
Stage #1: CYANAMID With potassium hydroxide In acetone for 0.25h; Stage #2: carbon disulfide In acetone at 10 - 15℃; for 2h; Stage #3: dimethyl sulfate at 40 - 45℃; for 6h;	93%
Yield given. Multistep reaction;

methylene chloride (74-87-3) + Cyanimidokohlensaeure (35042-86-5) → dimethyl N-cyanodithioiminocarbonate (10191-60-3)

Conditions	Yield
In methanol 1.) 30 deg C, 58 min, 2.) 64 deg C, 1 h;	89%

carbon disulfide (75-15-0) + calcium cyanamide (156-62-7) + dimethyl sulfate (77-78-1) → dimethyl N-cyanodithioiminocarbonate (10191-60-3)

Conditions	Yield
Stage #1: carbon disulfide; calcium cyanamide With sodium carbonate In water at 40 - 45℃; for 5h; Stage #2: dimethyl sulfate at 0 - 20℃; for 2h;	82%

potassium cyanocarbonimidodithioate (13145-41-0) + dimethyl sulfate (77-78-1) → dimethyl N-cyanodithioiminocarbonate (10191-60-3)

Conditions	Yield
In methanol at 20℃;	75%

carbon disulfide (75-15-0) + CYANAMID (420-04-2) + methyl iodide (74-88-4) → dimethyl N-cyanodithioiminocarbonate (10191-60-3)

Conditions	Yield
Stage #1: CYANAMID With potassium hydroxide In water at 20℃; for 0.75h; Stage #2: carbon disulfide In water at 40℃; for 2h; Stage #3: methyl iodide In water at 20℃; Further stages.;	71%
Stage #1: CYANAMID With potassium hydroxide In water at 20℃; for 0.75h; Stage #2: carbon disulfide In water at 40℃; for 2h; Stage #3: methyl iodide In water at 20℃;	71%
Multistep reaction;

potassium S-methyl N-cyanocarbamodithioate (10191-61-4) + dimethyl sulfate (77-78-1) → dimethyl N-cyanodithioiminocarbonate (10191-60-3)

CN2S3(2-)*2K(1+) + dimethyl sulfate (77-78-1) → dimethyl N-cyanodithioiminocarbonate (10191-60-3)

potassium S-methyl N-cyanocarbamodithioate (10191-61-4) + methyl iodide (74-88-4) → dimethyl N-cyanodithioiminocarbonate (10191-60-3)

Conditions	Yield
In acetone

C5H8N2S2 (52173-97-4) + methyl iodide (74-88-4) → dimethyl N-cyanodithioiminocarbonate (10191-60-3)

Conditions	Yield
With tetraethylammonium bromide In acetonitrile for 10h; Mechanism; electrolysis from various N-cyanimidodithiocarbonic acid esters with Ag-anode, Pt-cathode and diaphragm;

methylene chloride (74-87-3) + cyanocarbonimidodithioic acid (108-04-3) → dimethyl N-cyanodithioiminocarbonate (10191-60-3)

Conditions	Yield
In methanol at 60℃; for 1.25h; Yield given;

methyl iodide (74-88-4) + N-cyano-dithiocarbamidacidic silver → dimethyl N-cyanodithioiminocarbonate (10191-60-3)

Conditions	Yield
With potassium

sodium methyl N-cyanodithioiminocarbonate → dimethyl N-cyanodithioiminocarbonate (10191-60-3)

Conditions	Yield
With dimethyl sulfate In water	24.2 g (88%)

cyanocarbonimidodithioic acid (108-04-3) + methyl iodide (74-88-4) → dimethyl N-cyanodithioiminocarbonate (10191-60-3)

Conditions	Yield
In ethanol

dimethyl sulfate (77-78-1) + disodium N-cyanodithioiminocarbonate → dimethyl N-cyanodithioiminocarbonate (10191-60-3)

Conditions	Yield
at -5 - 85℃; for 29h; Temperature;	203.16 g

Cysteamine (60-23-1) + dimethyl N-cyanodithioiminocarbonate (10191-60-3) → 2-(N-cyanoimino)thiazolidine (26364-65-8)

Conditions	Yield
In ethanol at 90℃; for 2h;	100%
In ethanol for 3h; Heating / reflux;	67.1%
In ethanol Heating;

(E)-3-Amino-3-[N'-(pyridine-4-carbonyl)-hydrazino]-acrylic acid ethyl ester (146255-38-1) + dimethyl N-cyanodithioiminocarbonate (10191-60-3) → 5-Amino-7-methylsulfanyl-3-pyridin-4-yl-[1,2,4]triazolo[4,3-c]pyrimidine-8-carboxylic acid ethyl ester (151049-72-8)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide for 0.5h; Ambient temperature;	100%

(E)-3-Amino-3-[N'-(4-nitro-benzoyl)-hydrazino]-acrylic acid ethyl ester (146255-37-0) + dimethyl N-cyanodithioiminocarbonate (10191-60-3) → 5-Amino-7-methylsulfanyl-3-(4-nitro-phenyl)-[1,2,4]triazolo[4,3-c]pyrimidine-8-carboxylic acid ethyl ester (151049-71-7)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide for 0.5h; Ambient temperature;	100%

dimethyl N-cyanodithioiminocarbonate (10191-60-3) + (+)-4(5)-[(2R,5S)-(5-aminomethyl)tetrahydrofuran-2-yl]imidazole (222419-35-4) → C11H15N5OS

Conditions	Yield
In methanol at 20℃; for 1.5h;	100%

4-HYDROXYPIPERIDINE (5382-16-1) + dimethyl N-cyanodithioiminocarbonate (10191-60-3) → methyl N-cyano-4-hydroxypiperidine-1-carbimidothioate (128367-60-2)

Conditions	Yield
In ethanol Heating;	100%
In ethanol at 65℃; for 2.5h;

4-(2-(trifluoromethyl)phenoxy)piperidine (824390-04-7) + dimethyl N-cyanodithioiminocarbonate (10191-60-3) → methyl N-cyano-[2-(trifluoromethyl)phenoxy]piperidine-1-carbimidothioate (936716-41-5)

Conditions	Yield
In ethanol Heating;	100%
In ethanol for 0.5h; Heating / reflux;

ethyl 2-sulfanylacetate (623-51-8) + dimethyl N-cyanodithioiminocarbonate (10191-60-3) → ethyl 4-amino-2-(methylthio)thiazol-5-carboxylate (39736-29-3)

Conditions	Yield
With diisopropylamine In N,N-dimethyl-formamide at 100℃; for 5h;	99%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 100℃;	89%
With triethylamine In N,N-dimethyl-formamide
With triethylamine In N,N-dimethyl-formamide at 100℃; for 2h;

2-<(1H-indol-3-ylmethyl)thio>ethanamine (78131-25-6) + dimethyl N-cyanodithioiminocarbonate (10191-60-3) → methyl N'-cyano-N-<2-<(1H-indol-3-ylmethyl)thio>ethyl>carbamimidothioate (78131-27-8)

Conditions	Yield
In ethanol for 16h; Ambient temperature;	99%

dimethyl N-cyanodithioiminocarbonate (10191-60-3) + benzyl alcohol (100-51-6) → methylthiol (74-93-1) + benzyloxycarbonylcyanamide potassium salt (50909-46-1)

Conditions	Yield
With potassium hydroxide 1.) 80-90 deg C, 48 h; 2.) 25-30 deg C 24 h;	A n/a B 99%

2-chlorobenzenesulfonamide (6961-82-6) + dimethyl N-cyanodithioiminocarbonate (10191-60-3) → methyl N'-cyano-N-[(2-chlorophenyl)sulfonyl]imidothiocarbamate (104667-65-4)

Conditions	Yield
Stage #1: 2-chlorobenzenesulfonamide; dimethyl N-cyanodithioiminocarbonate With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 15h; Stage #2: With hydrogenchloride In N,N-dimethyl-formamide at 20℃; for 8h;	99%

4-methoxy-benzylamine (2393-23-9) + dimethyl N-cyanodithioiminocarbonate (10191-60-3) → methyl N'-cyano-N-(4-methoxybenzyl)carbamimidothioate

Conditions	Yield
In ethanol at 10 - 20℃; for 3h;	99%

ethylenediamine (107-15-3) + dimethyl N-cyanodithioiminocarbonate (10191-60-3) → 2-cyanoimino-imidazolidine (36982-79-3)

Conditions	Yield
In chloroform at 25 - 27℃; for 3h;	98.9%

S,S-dimethylsulfodiimide (13904-95-5) + dimethyl N-cyanodithioiminocarbonate (10191-60-3) → 3-Cyan-1-(dimethylimino-λ6-sulfanyliden)-2-methylisothioharnstoff (111268-31-6)

Conditions	Yield
at 60℃;	98%

3-Amino-3-(ethoxycarbonyl-hydrazono)-propionic acid ethyl ester (116751-83-8) + dimethyl N-cyanodithioiminocarbonate (10191-60-3) → ethyl 2-<(cyanoimino(methylthio)methyl)amino>-6-(2-ethoxycarbonylhydrazino)-4-methylthio-5-pyrimidinecarboxylate (151049-84-2)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide for 5h; Ambient temperature;	98%

(2-hydroxyethyl)(methyl)amine (109-83-1) + dimethyl N-cyanodithioiminocarbonate (10191-60-3) → 2-cyanoimido-3-methyl-1,3-oxazolidine (467250-55-1)

Conditions	Yield
With sodium hydroxide In diethyl ether at 20℃; for 36h;	98%

(E)-3-Amino-3-(N'-phenylacetyl-hydrazino)-acrylic acid ethyl ester (146255-34-7) + dimethyl N-cyanodithioiminocarbonate (10191-60-3) → 5-Amino-3-benzyl-7-methylsulfanyl-[1,2,4]triazolo[4,3-c]pyrimidine-8-carboxylic acid ethyl ester (151049-68-2)

Conditions	Yield
In dimethyl sulfoxide; toluene for 0.5h; Heating;	97%

2,4,6-triisopropylbenzene sulfonamide (105536-22-9) + dimethyl N-cyanodithioiminocarbonate (10191-60-3) → methyl N'-cyano-N-[(2,4,6-triisopropylphenyl)sulfonyl]imidothiocarbamate (104667-70-1)

Conditions	Yield
Stage #1: 2,4,6-triisopropylbenzene sulfonamide; dimethyl N-cyanodithioiminocarbonate With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 15h; Stage #2: With hydrogenchloride In N,N-dimethyl-formamide at 20℃; for 8h;	97%

benzothiophene-2-acetonitrile (75444-80-3) + dimethyl N-cyanodithioiminocarbonate (10191-60-3) → 3-(methylthio)-1-imino-pyrido[6,1-a]benzothiazol-4-carbonitrile

Conditions	Yield
With potassium hydroxide In 1,4-dioxane at 20℃; for 1h;	97%

4-Amidinobenzamide (54050-86-1) + dimethyl N-cyanodithioiminocarbonate (10191-60-3) → 4-amino-6-(4-carbamoylphenyl)-2-methylthio-1,3,5-triazine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol at 65℃;	96%

7-chloro-3-oxatricyclo[7.3.1.05,13]trideca-1(13),5,7,9,11-pentaene-8-carboximidamide (959766-46-2) + dimethyl N-cyanodithioiminocarbonate (10191-60-3) → 4-{7-chloro-3-oxatricyclo[7.3.1.05,13]trideca-1(13),5,7,9,11-pentaen-8-yl}-6-(methylsulfanyl)-1,3,5-triazin-2-amine (959766-47-3)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol at 20℃; for 3h; Heating / reflux;	96%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran Reflux;	90%
With ethanol; N-ethyl-N,N-diisopropylamine for 3h; Reflux;	88%

Glycyl-(S)-phenylalanine tert-butyl ester (16874-18-3) + dimethyl N-cyanodithioiminocarbonate (10191-60-3) → C18H24N4O3S (118534-61-5)

Conditions	Yield
In ethanol for 12h; Heating;	95%

2-mercaptoethylamine hydrochloride (156-57-0) + dimethyl N-cyanodithioiminocarbonate (10191-60-3) → 2-(N-cyanoimino)thiazolidine (26364-65-8)

Conditions	Yield
In ethanol for 6h; Heating;	95%
With sodium carbonate In water at 10 - 20℃; for 2h; Product distribution / selectivity;	93%
With sodium hydrogencarbonate In water at 10 - 20℃; for 3h; Product distribution / selectivity;	92%

3-Amino-3-(ethoxycarbonyl-hydrazono)-propionic acid ethyl ester (116751-83-8) + dimethyl N-cyanodithioiminocarbonate (10191-60-3) → 5-amino-2,3-dihydro-8-ethoxycarbonyl-7-methylthio-1,2,4-triazolo<4,3-c>pyrimidine-3-one (151049-86-4)

Conditions	Yield
In dimethyl sulfoxide; toluene for 0.5h; Heating;	95%

(E)-3-Amino-3-(N'-benzoyl-hydrazino)-acrylic acid ethyl ester (146255-36-9) + dimethyl N-cyanodithioiminocarbonate (10191-60-3) → 2-Amino-4-(N'-benzoyl-hydrazino)-6-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester (151049-63-7)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide for 0.75h; Ambient temperature;	95%

dimethyl N-cyanodithioiminocarbonate (10191-60-3) → C3H3N2OS(1-)*K(1+)

Conditions	Yield
With potassium hydroxide In acetone for 6h; Heating;	95%

5'-amino-5'-deoxythymidine (25152-20-9) + dimethyl N-cyanodithioiminocarbonate (10191-60-3) → 1-cyano-3-(5'-deoxythymidin-5'-yl)-2-methylisothiourea

Conditions	Yield
In ethanol for 25h;	95%

L-cysteine ethyl ester hydrochloride (868-59-7) + dimethyl N-cyanodithioiminocarbonate (10191-60-3) → (R)-2-[(Z)-Cyanoimino]-thiazolidine-4-carboxylic acid ethyl ester (258822-90-1)

Conditions	Yield
With triethylamine In ethanol Cyclization;	95%

(1S,2R)-1-amino-2-indanol (7480-35-5, 13286-59-4, 74165-73-4, 126456-43-7, 136030-00-7, 140632-19-5, 140632-20-8) + dimethyl N-cyanodithioiminocarbonate (10191-60-3) → [(3aS,8aR)-3,3a,8,8a-tetrahydro-2H-indenol[1,2-d][1,3]oxazol-2-ylidene]cyanamide (404942-39-8)

Conditions	Yield
In ethanol Heating;	95%

3-chloro-benzenesulfonamide (17260-71-8) + dimethyl N-cyanodithioiminocarbonate (10191-60-3) → methyl N'-cyano-N-[(3-chlorophenyl)sulfonyl]imidothiocarbamate (125002-83-7)

Conditions	Yield
Stage #1: 3-chloro-benzenesulfonamide; dimethyl N-cyanodithioiminocarbonate With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 15h; Stage #2: With hydrogenchloride In N,N-dimethyl-formamide at 20℃; for 8h;	95%

2-(5-chloro-benzothiazol-2-ylsulfanyl)-ethylamine (108106-65-6) + dimethyl N-cyanodithioiminocarbonate (10191-60-3) → N-(5-chlorobenzothiazol-2-yl)thioethyl-N'-cyano-S-methylisourea

Conditions	Yield
In ethanol	95%

Upstream product

• 75-15-0 carbon disulfide 
• 156-62-7 calcium cyanamide 
• 77-78-1 dimethyl sulfate 
• 108-04-3 cyanocarbonimidodithioic acid 
• 74-88-4 methyl iodide 
• 74-87-3 methylene chloride 
• 35042-86-5 Cyanimidokohlensaeure 
• 52173-97-4 C₅H₈N₂S₂ 
• 420-04-2 CYANAMID 
• 13145-41-0 potassium cyanocarbonimidodithioate 
• 10191-61-4 potassium S-methyl N-cyanocarbamodithioate 

Downstream Products

• 65159-22-0 (4-ethyl-3-phenyl-4H-[1,2,4]oxadiazol-5-ylidene)-cyanamide 
• 65159-21-9 (3,4-diphenyl-4H-[1,2,4]oxadiazol-5-ylidene)-cyanamide 
• 586965-23-3 N.S-Dimethyl-N-cyanmethyl-N'-cyan-isothioharnstoff 
• 47165-11-7 6,6'-Dimethyl-2,2'-imino-bis- 
• 59566-71-1 (4-oxo-6-phenyl-4H-[1,3,5]thiadiazin-2-yl)-dithiocarbonimidic acid dimethyl ester 
• 15760-26-6 3-cyano-2-methylisothiourea 
• 55864-39-6 5-Amino-3-methylthio-1,2,4-oxadiazol 
• 86123-54-8 1-(1-Benzyl-4-piperidinyl)-3-cyan-2-methylisothioharnstoff 
• 74-93-1 methylthiol 
• 24771-25-3 dimethyl (N-cyanoimido)carbonate 
• 104692-80-0 C₉H₉N₃O₂S₂ 
• 104667-66-5 C₁₀H₁₁N₃O₂S₂ 
• 73279-12-6 N-Cyano-S-methyl-N'-<3-<3-(1-piperidinylmethyl)-phenoxy>-propyl>-isothioharnstoff 
• 111971-58-5 2-amino-5-cyano-6-(methylthio)-4(3H)-pyrimidinethione 

Relevant articles and documents

An improved preparation of S,S′-dimethyl N-cyanodithioiminocarbonate

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Thiazole amide compound as well as preparation and application thereof

The invention discloses a thiazole amide compound as well as preparation and application thereof. The structural general formula of the thiazole amide compound is shown in the specification, wherein an X group is selected from methylene (-CH2-), oxygen (O), amino (-NH), N-methyl (-NCH3-), N-isopropyl (-N-CH (CH3) 2) and sulfur (S), and the R group is selected from phenyl, p-methylphenyl, p-nitrophenyl, p-fluorophenyl, p-hydroxyphenyl, p-methoxyphenyl, 3-chloro-2-methylphenyl and 5-chloro-2-methylphenyl. The thiazole amide compound disclosed by the invention has excellent antibacterial activityon valsa mali, fusarium oxysporum, colletotrichum citri and the like, and can be used for preventing and treating crop diseases.

A preparation method of the emetic (by machine translation)

The invention relates to the field of organic synthetic technology, in particular to a emetic preparation method, comprises the following steps: S1, 3 - methoxy methyl acrylic acid methyl ester preparation; S2, synthesis of [...]; S3, is the synthesis of third zuo; S4, and aldehyde; S5, closed-loop. This invention adopts the single melamine as the synthetic starting material, greatly reducing the cost, dicyandiamide as to effectively solve the problem of lack of raw material sources; solved in the prior art long reaction time, the reaction condition is sensitive, harsh, side reaction are numerous and complex, the use of expensive or difficult to prepare sodium of other reagents, reactions caused low overall yield, the product quality is poor, so that the synthesis process technology of the route is more stable, good reproducibility, high yield, the product quality is good, content can be up to 99.5%, the yield can reach 85.6%, has higher economic benefits. (by machine translation)