Pyridine → 2-Acetamido-4-chloromethylthiazole

N-(4-(chloromethyl)thiazol-2-yl)acetamide was prepared following a literature procedure (Silberg, A.; Frenkel, Z.; Bull. Soc. Chim. Fr.; 1967; 2235-2238). A suspension of 1-acetylisothiourea (3.55 g, 0.03 mol), 1,3-dichloropropan-2-one (3.8 g, 0.03 mol) and pyridine (1.96 g, 2 ml, 0.025 mol) in acetone (10 ml) was heated at 100 C in an oil bath for 20 minutes. A flocculent white solid formed. After cooling to room temperature, the reaction mixture was filtered to collect the white solid. The filtrate was evaporated, and the resulting residue was taken into water resulted in a white suspension which was stirred for a couple of minutes. The suspension was filtered. The collected solid was washed with water, dried under vacuum and combined with the above-mentioned white solid to give 2.89 g (51% yield) of N-(4-(chloromethyl)thiazol-2-yl)acetamide. LC/MS m/z 191.05, 193.05 (M+H)+); HPLC Rt: 1.71 min.

1. customN-(4-(chloromethyl)thiazol-2-yl)acetamide was prepared
2. temperaturewas heated at 100 C in an oil bath for 20 minutes
3. customA flocculent white solid formed
4. filtrationthe reaction mixture was filtered
5. customto collect the white solid
6. customThe filtrate was evaporated
7. customresulted in a white suspension which
8. filtrationThe suspension was filtered
9. washThe collected solid was washed with water
10. customdried under vacuum

ORD record

ord-3efb35093a1c433a942b74da34ba8811

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07361654B2