Water → HCID 21866466, compound

Participants

Reaction Conditions

Reaction Steps

75.0 g (0.29 mol) of BOC-protected thiazolecarboxamide (VI) were suspended in 524 ml of dichloromethane and, at from −5° to 0° C., admixed with 78.9 g (0.78 mol) of triethylamine and 79.5 g (0.38 mol) of trifluoroacetic anhydride. The mixture was stirred for one hour and allowed to warm to 20-25° C., 1190 ml of water were added and the phases were separated. 160 ml of 5-6 N isopropanolic HCl were added to the organic phase, the mixture was heated to the boil for 3 h, stirred at 20-25° C. overnight and cooled to from −5 to 0° C. for 2.5 h, and the solid was filtered off. It was washed with dichloromethane and dried. This gave 48.1 g of 2-aminomethyl-4-cyanothiazole of a purity by HPLC of 99.4 area %, which corresponds to a yield of 94.3% for these two steps.

Provenance & Evidence