2-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1) → HCID 59570821, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-amino-4-chloromethyl-thiazole hydrochloride (27.8 g, 0.15 mol), N,O-dimethylhydroxylamine hydrochloride (87.8 g, 0.90 mol), and anhydrous THF (300 mL) was rapidly stirred and DIPEA (157 mL, 0.90 mol) was added. The resulting mixture was heated at 60° C. for 10-15 hours. The mixture was cooled in an ice/salt bath and the solid byproduct (DIPEA hydrochloride) was removed by filtration and washed with cold THF (300 mL). The combined filtrate was concentrated to afford the N-(2-amino-thiazol-4-ylmethyl)-O,N-dimethyl-hydroxylamine as a dark oil (31 g, >100% theory), which partially crystallized on standing. This product was used in the next step without further purification.

Provenance & Evidence