2-Amino-4-chloromethythiazole hydrochloride

Uses

2-Amino-4-chloromethyl thiazole hydrochloride is an α-thiophene derivative, which is widely used in synthetic medicines, pesticides, dyes, chemical reagents, polymer additives, etc.

Synthesis

The general procedure for the synthesis of 2-amino-4-chloromethylthiazole hydrochloride from the compound (CAS: 17356-08-0) and 1,3-dichloroacetone was carried out as follows: a mixture of 1,3-dichloroacetone (380.9 g, 3 mol), thiourea (228.3 g, 3 mol), and isopropanol (3.6 L) was stirred at 40 °C in an inert atmosphere until a clarified solution. Subsequently, the reaction mixture was continued to be stirred at room temperature overnight to induce crystallization of the product. Upon completion of the reaction, the mixture was cooled to -20 °C to promote complete crystallization and the product was subsequently isolated by filtration. The resulting crystals were washed with cold isopropanol (0.4 L) and finally dried under vacuum to afford 2-amino-4-chloromethylthiazole hydrochloride as white crystals (408 g, 73.5% yield).

References

[1] Journal of Medicinal Chemistry, 2016, vol. 59, # 21, p. 9686 - 9720
[2] Patent: WO2009/15193, 2009, A1. Location in patent: Page/Page column 44
[3] Bollettino Chimico Farmaceutico, 1995, vol. 134, # 11, p. 639 - 643
[4] Patent: WO2008/11191, 2008, A1. Location in patent: Page/Page column 36
[5] Patent: EP3018125, 2016, A1. Location in patent: Paragraph 0753-0755