26364-65-8

Basic information

• Product Name: 2-Cyaniminothiazolidine
• Synonyms: 2-CYANOIMINO-1,3-THIAZOLIDINE;2-CYANOIMINO THIAZOLIDINE;2-CYANIMINOTHIAZOLIDINE;2-CYANIMINOTHIAZOLIDINE (CIT);[(1,3-thiazolidin-2-ylidene)aMino]carbonitrile;2-CyanoiMinoradical-1,3-thiazolidine;N-(4,5-dihydrothiazol-2-yl)cyanaMide;2-cyanoiMino-aMino-1,3-thiazolidine
• CAS NO: 26364-65-8
• Molecular Formula: C₄H₅N₃S
• Molecular Weight: 127.17
• EINECS: 427-720-1
• Mol File: 26364-65-8.mol
• Article Data: 20

Chemical Properties

• Melting Point: 156-157 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• Boiling Point: 227.6 °C at 760 mmHg
• Flash Point: 91.5 °C
• Appearance: /
• Density: 1.43 g/cm³
• Vapor Pressure: 0.0768mmHg at 25°C
• Refractive Index: 1.698
• Storage Temp.: 2-8°C
• PKA: 3.95±0.10(Predicted)
• CAS DataBase Reference: 2-Cyaniminothiazolidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyaniminothiazolidine(26364-65-8)
• EPA Substance Registry System: 2-Cyaniminothiazolidine(26364-65-8)

Safety Data

• Hazardous Substances Data: 26364-65-8(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 24, p. 275, 1987 DOI: 10.1002/jhet.5570240153

InChI:InChI=1/C4H5N3S/c5-3-7-4-6-1-2-8-4/h1-2H2,(H,6,7)

Synthetic route

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;

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%

sodium acetate (127-09-3) + 3-Methanesulfonyl-thiazolidin-(2E)-ylidene-cyanamide (132433-56-8) → 2-(N-cyanoimino)thiazolidine (26364-65-8) + 3-Acetyl-thiazolidin-(2Z)-ylidene-cyanamide

Conditions	Yield
In N,N-dimethyl-formamide at 80℃;	A 6% B 85%

propan-1-ol (71-23-8) + 3-Methanesulfonyl-thiazolidin-(2E)-ylidene-cyanamide (132433-56-8) → 3-Propyl-thiazolidin-(2E)-ylidene-cyanamide (140483-44-9) + 2-(N-cyanoimino)thiazolidine (26364-65-8)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 80℃;	A 83% B 16%

ethanol (64-17-5) + 3-Methanesulfonyl-thiazolidin-(2E)-ylidene-cyanamide (132433-56-8) → 3-Ethyl-thiazolidin-(2E)-ylidene-cyanamide (97538-34-6) + 2-(N-cyanoimino)thiazolidine (26364-65-8)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 80℃;	A 82% B 13%

3-Methanesulfonyl-thiazolidin-(2E)-ylidene-cyanamide (132433-56-8) + cyclohexanol (108-93-0) → 2-(N-cyanoimino)thiazolidine (26364-65-8) + 3-Cyclohexyl-thiazolidin-(2Z)-ylidene-cyanamide

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 80℃;	A 81% B 6%

methanol (67-56-1) + 3-Methanesulfonyl-thiazolidin-(2E)-ylidene-cyanamide (132433-56-8) → 3-Methyl-thiazolidin-(2E)-ylidene-cyanamide (97538-33-5) + 2-(N-cyanoimino)thiazolidine (26364-65-8)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 80℃;	A 79% B 16%
With sodium hydride In N,N-dimethyl-formamide at 80℃; Mechanism; Product distribution; effect of different alcohols;	A 79% B 16%

ethanol (64-17-5) + 3-(3-Nitro-benzenesulfonyl)-thiazolidin-(2Z)-ylidene-cyanamide → 3-Ethyl-thiazolidin-(2E)-ylidene-cyanamide (97538-34-6) + 2-(N-cyanoimino)thiazolidine (26364-65-8)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 80℃;	A 79% B 10%

3-Methanesulfonyl-thiazolidin-(2E)-ylidene-cyanamide (132433-56-8) + butyric acid (107-92-6) → 2-(N-cyanoimino)thiazolidine (26364-65-8) + 3-Butyryl-thiazolidin-(2Z)-ylidene-cyanamide

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 80℃;	A 8% B 79%

3-dimethoxymethyl-2-(N-cyanoimino)thiazolidine (160314-52-3) + benzyl alcohol (100-51-6) → benzyl formate dimethyl acetal (27591-56-6) + 2-(N-cyanoimino)thiazolidine (26364-65-8)

Conditions	Yield
In tetrahydrofuran Heating;	A 76% B n/a

3-(imidazol-4-ylmethyl)-2-(N-cyanoimino)thiazolidine (144989-88-8) → 2-(N-cyanoimino)thiazolidine (26364-65-8)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 80℃;	72%

3-Methanesulfonyl-thiazolidin-(2E)-ylidene-cyanamide (132433-56-8) + propionic acid (802294-64-0) → 2-(N-cyanoimino)thiazolidine (26364-65-8) + 3-Propionyl-thiazolidin-(2Z)-ylidene-cyanamide

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 80℃;	A 8% B 71%

N-cyano-S-methyl-S'-<(5-methyl-1H-imidazol-4-yl)methyl>-dithiocarbamate (76234-82-7) → 2-(N-cyanoimino)thiazolidine (26364-65-8)

Conditions	Yield
With ethyleneimine In ethanol for 15h; Ambient temperature;	70%

3-Methanesulfonyl-thiazolidin-(2E)-ylidene-cyanamide (132433-56-8) + isopropyl alcohol (67-63-0) → 3-Isopropyl-thiazolidin-(2E)-ylidene-cyanamide (97538-41-5) + 2-(N-cyanoimino)thiazolidine (26364-65-8)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 80℃;	A 24% B 68%

3-Methanesulfonyl-thiazolidin-(2E)-ylidene-cyanamide (132433-56-8) + benzyl alcohol (100-51-6) → 3-benzylthiazolidin-2-ylidenecyanamide (94777-00-1) + 2-(N-cyanoimino)thiazolidine (26364-65-8)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 80℃;	A 66% B 29%

3-Methanesulfonyl-thiazolidin-(2E)-ylidene-cyanamide (132433-56-8) + benzoic acid (65-85-0) → 2-(N-cyanoimino)thiazolidine (26364-65-8) + 3-Benzoyl-thiazolidin-(2Z)-ylidene-cyanamide

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 80℃;	A 14% B 61%

ethanol (64-17-5) + 3-(4-Nitro-benzenesulfonyl)-thiazolidin-(2Z)-ylidene-cyanamide → 3-Ethyl-thiazolidin-(2E)-ylidene-cyanamide (97538-34-6) + 2-(N-cyanoimino)thiazolidine (26364-65-8)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 80℃;	A 24% B 59%

sodium methyl N-cyanodithioiminocarbonate + 2-chloroethanamine hydrochloride (870-24-6) → 2-(N-cyanoimino)thiazolidine (26364-65-8)

Conditions	Yield
With sodium hydroxide In water at 70 - 75℃; for 4h; pH=6.3 - 6.8; Concentration; Temperature; pH-value;	56.9%

ethanol (64-17-5) + 3-(4-Chloro-benzenesulfonyl)-thiazolidin-(2E)-ylidene-cyanamide (132433-57-9) → 3-Ethyl-thiazolidin-(2E)-ylidene-cyanamide (97538-34-6) + 2-(N-cyanoimino)thiazolidine (26364-65-8)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 80℃;	A 56% B 9%

3-(imidazol-4-ylmethyl)-2-(N-cyanoimino)thiazolidine (144989-88-8) + isopropyl alcohol (67-63-0) → C11H17N5OS (144989-90-2) + 2-(N-cyanoimino)thiazolidine (26364-65-8)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide	A 27% B 50%

dimethyl (N-cyanoimido)carbonate (24771-25-3) + Cysteamine (60-23-1) → 2-(N-cyanoimino)thiazolidine (26364-65-8)

Conditions	Yield
With sodium hydroxide at 20℃; Cyclization;	48%

ethanol (64-17-5) + 3-(4-Methoxy-benzenesulfonyl)-thiazolidin-(2Z)-ylidene-cyanamide → 3-Ethyl-thiazolidin-(2E)-ylidene-cyanamide (97538-34-6) + 2-(N-cyanoimino)thiazolidine (26364-65-8)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 80℃;	A 19% B 38%

ethanol (64-17-5) + 3-(2-Nitro-benzenesulfonyl)-thiazolidin-(2Z)-ylidene-cyanamide → 3-Ethyl-thiazolidin-(2E)-ylidene-cyanamide (97538-34-6) + 2-(N-cyanoimino)thiazolidine (26364-65-8)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 80℃;	A 20% B 33%

ethanol (64-17-5) + 3-(Toluene-4-sulfonyl)-thiazolidin-(2E)-ylidene-cyanamide (97097-66-0) → 3-Ethyl-thiazolidin-(2E)-ylidene-cyanamide (97538-34-6) + 2-(N-cyanoimino)thiazolidine (26364-65-8)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 80℃;	A 22% B 7%

2-mercaptoethylamine hydrochloride (156-57-0) + N-cyanodiphenylcarbonimidate (79463-77-7) → 2-(N-cyanoimino)thiazolidine (26364-65-8)

Conditions	Yield
With sodium hydroxide In methanol; water Heating;	1 g

PCM-0102378 (260553-15-9) + 2-(N-cyanoimino)thiazolidine (26364-65-8) → C16H16ClF3N6OS

Conditions	Yield
With triethylamine In acetonitrile for 2h; Reflux;	96%

2-(N-cyanoimino)thiazolidine (26364-65-8) → C8H16N10S2 (131505-06-1)

Conditions	Yield
With hydrazine hydrate In ethanol Heating;	90%

1-bromomethyl-3-methyl-benzene (620-13-3) + 2-(N-cyanoimino)thiazolidine (26364-65-8) → 3-(3-methylbenzyl)thiazolidin-2-ylidenecyanamide

Conditions	Yield
With sodium hydroxide In water; acetonitrile at 20℃; for 8h;	89.7%

2-chloro-5-(chloromethyl)pyridine (70258-18-3) + 2-(N-cyanoimino)thiazolidine (26364-65-8) → thiacloprid

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate In water at 60℃; for 4h; Reagent/catalyst; Temperature;	88.2%

4-Methylbenzyl bromide (104-81-4) + 2-(N-cyanoimino)thiazolidine (26364-65-8) → 3-(4-methylbenzyl)thiazolidin-2-ylidenecyanamide

Conditions	Yield
With sodium hydroxide In water; acetonitrile at 20℃; for 8h;	87.4%

2-(N-cyanoimino)thiazolidine (26364-65-8) + 4-cyanobenzyl bromide (17201-43-3) → 3-(4-cyanobenzyl)thiazolidin-2-ylidenecyanamide

Conditions	Yield
With sodium hydroxide In water; acetonitrile at 20℃; for 8h;	87.3%

4-Fluorobenzyl bromide (459-46-1) + 2-(N-cyanoimino)thiazolidine (26364-65-8) → 3-(4-fluorobenzyl)thiazolidin-2-ylidenecyanamide

Conditions	Yield
With sodium hydroxide In water; acetonitrile at 20℃; for 8h;	87.2%

2-(N-cyanoimino)thiazolidine (26364-65-8) + 3-(bromomethyl)benzonitrile (28188-41-2) → 3-(3-cyanobenzyl)thiazolidin-2-ylidenecyanamide

Conditions	Yield
With sodium hydroxide In water; acetonitrile at 20℃; for 8h;	86.1%

methanesulfonyl chloride (124-63-0) + 2-(N-cyanoimino)thiazolidine (26364-65-8) → 3-Methanesulfonyl-thiazolidin-(2E)-ylidene-cyanamide (132433-56-8)

Conditions	Yield
With triethylamine In chloroform	86%
With triethylamine In chloroform Ambient temperature;	86%

C11H11ClN2O2 + 2-(N-cyanoimino)thiazolidine (26364-65-8) → C15H15N5O2S

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 4h;	86%

2-(N-cyanoimino)thiazolidine (26364-65-8) + 2-(bromomethyl)benzonitrile (22115-41-9) → 3-(2-cyanobenzyl)thiazolidin-2-ylidenecyanamide

Conditions	Yield
With sodium hydroxide In water; acetonitrile at 20℃; for 8h;	85.7%

2-methylbenzyl bromide (89-92-9) + 2-(N-cyanoimino)thiazolidine (26364-65-8) → 3-(2-methylbenzyl)thiazolidin-2-ylidenecyanamide

Conditions	Yield
With sodium hydroxide In water; acetonitrile at 20℃; for 8h;	85.4%

1-(bromomethyl)-4-(1,1-dimethylethyl)benzene (18880-00-7) + 2-(N-cyanoimino)thiazolidine (26364-65-8) → 3-(4-tert-butylbenzyl)thiazolidin-2-ylidenecyanamide

Conditions	Yield
With sodium hydroxide In water; acetonitrile at 20℃; for 8h;	85.4%

bromocyane (506-68-3) + 2-(N-cyanoimino)thiazolidine (26364-65-8) → 3-cyano-2-(N-cyanoimino)thiazolidine (515856-60-7)

Conditions	Yield
Stage #1: 2-(N-cyanoimino)thiazolidine With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: bromocyane In tetrahydrofuran at 20℃; for 3h;	85%

1-(Bromomethyl)-3-fluorobenzene (456-41-7) + 2-(N-cyanoimino)thiazolidine (26364-65-8) → 3-(3-fluorobenzyl)thiazolidin-2-ylidenecyanamide

Conditions	Yield
With sodium hydroxide In water; acetonitrile at 20℃; for 8h;	84.9%

2-(N-cyanoimino)thiazolidine (26364-65-8) + 1-Bromo-2-bromomethyl-benzene (3433-80-5) → 3-(2-bromobenzyl)thiazolidin-2-ylidenecyanamide

Conditions	Yield
With sodium hydroxide In water; acetonitrile at 20℃; for 8h;	84.3%

4-methoxy-phenyl-sulphonyl chloride (98-68-0) + 2-(N-cyanoimino)thiazolidine (26364-65-8) → 3-(4-Methoxy-benzenesulfonyl)-thiazolidin-(2Z)-ylidene-cyanamide

Conditions	Yield
With triethylamine In chloroform Ambient temperature;	84%

o-fluorobenzyl bromide (446-48-0) + 2-(N-cyanoimino)thiazolidine (26364-65-8) → 3-(2-fluorobenzyl)thiazolidin-2-ylidenecyanamide

Conditions	Yield
With sodium hydroxide In water; acetonitrile at 20℃; for 8h;	83.6%

5-(chloromethyl)-3-(2-(2,2-difluoroethoxy)phenyl)-1,2,4-oxadiazole + 2-(N-cyanoimino)thiazolidine (26364-65-8) → 5-((2-cyanoimino-1,3-thiazolidine)-N-methyl)-3-(2-(2,2-difluoroethoxy)phenyl)-1,2,4-oxadiazole

Conditions	Yield
Stage #1: 2-(N-cyanoimino)thiazolidine With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 0.5h; Stage #2: 5-(chloromethyl)-3-(2-(2,2-difluoroethoxy)phenyl)-1,2,4-oxadiazole In N,N-dimethyl-formamide for 4h;	82.1%

p-toluenesulfonyl chloride (98-59-9) + 2-(N-cyanoimino)thiazolidine (26364-65-8) → 3-(Toluene-4-sulfonyl)-thiazolidin-(2E)-ylidene-cyanamide (97097-66-0)

Conditions	Yield
With triethylamine In chloroform	81%
With triethylamine In chloroform Ambient temperature;	81%

4-chlorobenzyl bromide (622-95-7) + 2-(N-cyanoimino)thiazolidine (26364-65-8) → 3-(4-chlorobenzyl)thiazolidin-2-ylidenecyanamide (94777-01-2)

Conditions	Yield
With sodium hydroxide In water; acetonitrile at 20℃; for 8h;	80.2%

5-chloromethyl-3-(2,6-difluorophenyl)-1,2,4-oxadiazole + 2-(N-cyanoimino)thiazolidine (26364-65-8) → C13H9F2N5OS

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 4h;	80%

4-chlorobenzenesulfonyl chloride (98-60-2) + 2-(N-cyanoimino)thiazolidine (26364-65-8) → 3-(4-Chloro-benzenesulfonyl)-thiazolidin-(2E)-ylidene-cyanamide (132433-57-9)

Conditions	Yield
With triethylamine In chloroform	79%
With triethylamine In chloroform Ambient temperature;	79%

Upstream product

• 64-17-5 ethanol 
• 132433-56-8 3-Methanesulfonyl-thiazolidin-(2E)-ylidene-cyanamide 
• 97097-66-0 3-(Toluene-4-sulfonyl)-thiazolidin-(2E)-ylidene-cyanamide 
• 132433-57-9 3-(4-Chloro-benzenesulfonyl)-thiazolidin-(2E)-ylidene-cyanamide 
• 100-51-6 benzyl alcohol 
• 108-93-0 cyclohexanol 
• 107-92-6 butyric acid 
• 24771-25-3 dimethyl (N-cyanoimido)carbonate 
• 60-23-1 Cysteamine 
• 156-57-0 2-mercaptoethylamine hydrochloride 
• 10191-60-3 dimethyl N-cyanodithioiminocarbonate 
• 51605-33-5 4-methyl-5-chloromethyl-imidazole hydrochloride 
• 21729-98-6 N-cyanocarbonimidic acid methyl ester 
• 65-85-0 benzoic acid 

Downstream Products

• 258822-89-8 3-Phenylsulfenyl-2-(N-cyanoimino)thiazolidine 
• 449813-82-5 3-(diphenylphosphono)-2-(N-cyanoimino)thiazolidine 

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