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

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).

1. concentrationThe resulting suspension was concentrated to dryness in vacuo
2. additionEthanol (1.2 L) was added
3. stirringthe mixture was stirred for 3 h
4. customThe insolubles were removed by filtration
5. concentrationthe filtrate was concentrated to 500 mL
6. additionHeptanes (1.5 L) were slowly added
7. customresulting in the formation of a white precipitate
8. customThis was isolated by filtration
9. washwashed with heptane
10. customdried in vacuo

ORD record

ord-1699e11a7dfe4df59ec6abb6a4c89a62

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08148380B2