| Identification | Back Directory | [Name]
2-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole | [CAS]
78441-62-0 | [Synonyms]
Einecs 278-909-9
Nizatidine intermediate
Nizatidine EP IMpurity D
Nizatidine Impurity 4(Nizatidine EP Impurity D)
2-(2-(Dimethylaminomethyl-4-thiazol)methylthio)ethylamine
2-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazol
2-(Dimethylaminomethyl)-4-(2-Aminoethylthionmethyl)Thiazole
4-(2-aminoethylthiomethyl)-1,3-thiazol-2-ylmethyldimethylamine
2-[[2-[(dimethylamino)methyl]-4-thiazolyl]methylthio]ethanamine
2-(((2-((methylamino)methyl)thiazol-4-yl)methyl)thio)ethanamine
2-(((2-((Dimethylamino)methyl)thiazol-4-yl)methyl)thio)ethanamine
2-(((2-((DIMETHYLAMINO)METHYL)THIAZOL-4- L)METHYL)THIO)ETHANAMINE
4-[[(2-aminoethyl)thio]methyl]-N,N-dimethylthiazole-2-methylamine
4-[[(2-Aminoethyl)thio]methyl]-N,N-dimethyl-2-thiazolemethanamine
2-Thiazolemethanamine, 4-(((2-aminoethyl)thio)methyl)-N,N-dimethyl-
2-[(N,N-Dimethylamino)methyl]-4-[(2-aminoethyl)thiomethyl] thiazole
2-[[2-(Dimethylaminomethyl)-1,3-Thiazol-4-Yl]Methylsulfanyl]Ethanamine | [EINECS(EC#)]
278-909-9 | [Molecular Formula]
C9H17N3S2 | [MDL Number]
MFCD08703310 | [MOL File]
78441-62-0.mol | [Molecular Weight]
231.38 |
| Chemical Properties | Back Directory | [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) | [form ]
Oil to Thick Oil | [pka]
8.83±0.10(Predicted) | [color ]
Yellow to Very Dark Red |
| Hazard Information | Back Directory | [Chemical Properties]
Brown Liquid | [Uses]
2-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole (Nizatidine EP Impurity D) is a Nizatidine intermediate. | [Uses]
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 |
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