Water → HCID 21866466, compound

Participants

Reaction Conditions

Reaction Steps

Boc-2-aminomethylthiazole-4-carboxamide (75.0 g, 0.29 mol) was suspended in 524 ml of methylene chloride and, at from −5 to 0° C., admixed with triethylamine (78.9 g, 0.78 mol) and 79.5 g (0.38 mol) of trifluoroacetic anhydride. The mixture was stirred for another 1 h and then 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 hydrochloric acid 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, washed with methylene chloride and dried. This gave 48.1 g of 2-aminomethyl-4-cyanothiazole of an HPLC purity of 99.4 area %, which corresponds to a yield over these two steps of 94.3%.

Provenance & Evidence