Thioacetamide → Ethyl 2-(2-methylthiazol-5-yl)acetate

A mixture of 28.7 g of ethyl 3-bromo-4-oxo-butyrate, 300 ml of dichloroethane and 11.2 g of thioacetamide was refluxed for 10 hours with stirring while replacing the dichloroethane that distilled to keep the volume constant and then the mixture was cooled to room temperature. The mixture was evaporated to dryness and the residue was dissolved in ethyl acetate. The solution was extracted with 2N hydrochloric acid and the pH of the aqueous extracts was made alkaline by addition of ammonium hydroxide. The mixture was extracted with ethyl acetate and the organic extract was washed with water, dried and evaporated to dryness to obtain 8.3 g of ethyl 2-methyl-5-thiazole acetate. The IR spectrum in CHCl3 showed ester C=O at 1737cm-1 and C=C and C=N at 1535cm-1.

1. temperaturewas refluxed for 10 hours
2. distillationthat distilled
3. customThe mixture was evaporated to dryness
4. dissolutionthe residue was dissolved in ethyl acetate
5. extractionThe solution was extracted with 2N hydrochloric acid
6. additionby addition of ammonium hydroxide
7. extractionThe mixture was extracted with ethyl acetate
8. extractionthe organic extract
9. washwas washed with water
10. customdried
11. customevaporated to dryness

ORD record

ord-2019cab32ea346b89823cb91605b7429

Source dataset

uspto-grants-1977_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04053618