2-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole Chemical Properties

Boiling point:

338.9±37.0 °C(Predicted)

Density 

1.182±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

pka

8.83±0.10(Predicted)

form 

Oil to Thick Oil

color 

Yellow to Very Dark Red

2-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole Usage And Synthesis

Chemical Properties

Brown Liquid

Uses

2-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole (Nizatidine EP Impurity D) is a Nizatidine intermediate.

Synthesis

General procedure for the synthesis of 2-(dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole from 2-mercaptoethylamine hydrochloride and 1,4-chloromethyl-2-dimethylaminothiazole hydrochloride: 2-aminoethanol hydrochloride (cysteamine hydrochloride, 520 g, 4.5 mol) was suspended in water (500 mL). This suspension was cooled to 5 °C and sodium hydroxide solution (45% w/w, 870 mL; 14.7 mol) was slowly added at 5-10 °C. Subsequently, hydroxylamine sulfate (100 g; 0.6 mol) was added to this suspension with continuous stirring. Another solution was prepared by dissolving 4-chloromethyl-2-dimethylaminomethylthiazole hydrochloride (1000 g; 4.43 mol) in water (1250 mL). The solution was slowly added to the above suspension while keeping the temperature below 10 °C and the reaction was continued at 10 °C for 1 hour. The reaction process was confirmed by qualitative HPLC monitoring. Upon completion of the reaction, the reaction mixture was diluted with water (2000 mL), heated to 40-45°C and extracted with toluene (2 x 2000 mL). The toluene extracts were combined and treated with activated charcoal at 40-45 °C for 30 min. The treated solution was filtered through a HYFLO bed to remove the activated carbon and the filtrate was evaporated at 60 °C under reduced pressure to remove toluene, resulting in 910 g of the target product in 88% yield.

References

[1] Patent: WO2004/69817, 2004, A1. Location in patent: Page 8

2-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole(78441-62-0)Related Product Information

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