1,3-Dichloroacetone → 2-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1)

Participants

Reaction Steps

To a solution of 1,3-dichloroacetone (150 g, 1.18 mol) in acetone (600 mL) was added a solution of thiourea (91.7 g, 1.23 mol) in acetone (3000 mL). The mixture was stirred overnight at room temperature. The resulting suspension was concentrated to dryness in vacuo. Ethanol (1.2 L) was added and the mixture was stirred for 3 h. The insolubles were removed by filtration and the filtrate was concentrated to 500 mL. Heptanes (1.5 L) were slowly added resulting in the formation of a white precipitate. This was isolated by filtration, washed with heptane and dried in vacuo to afford 4-(chloromethyl)thiazol-2-amine hydrochloride as a white solid (141.3 g, 0.76 mol, 64%). 1H NMR (DMSO-d6): δ 9.50 (bs, 2H); 7.00 (s, 1H); 4.68 (s, 2H).

Provenance & Evidence