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

Compound 200 was synthesized as shown in Scheme 8. Reaction of α,γ-dichloroacetone (15.9 mmol) with thiourea (15.9 mmol) in dry acetone (8 mL) afforded a white solid. The white solid was collected and stirred in anhydrous ethanol to remove insoluble isothiourea. To the ethanol filtrate, 25-30 mL of hexanes was added with stirring to afford 2-amino-4-chloromethylthiazole hydrochloride as a white crystalline solid. The resulting compound was further reacted with N,N-diethylamine in ethanol and neutralized with 20% sodium hydroxide to gave an intermediate. The intermediate reacted with DBD to yield the desired product.

1. customafforded a white solid
2. customThe white solid was collected
3. customto remove insoluble isothiourea
4. additionTo the ethanol filtrate, 25-30 mL of hexanes was added
5. stirringwith stirring

ORD record

ord-23d8fa28d30446dd8055d2dea72034fc

Source dataset

uspto-grants-2005_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06903133B2