Chloroacetone → 1-(2-Phenyl-1,3-thiazol-5-yl)ethan-1-one

A mixture of 10.0 g (72.9 mmol) of thiobenzamide and 17.4 g (146 mmol) dimethylformamide dimethyl acetal was stirred at room temperature for 2 hours. The volatiles were evaporated under reduced pressure. The residue was dissolved in ethanol (40 ml). To this solution was added 1.0 g (109 mmol) of chloroacetone and the mixture was stirred at room temperature for 3.5 hours. The reaction mixture was diluted with ethyl acetate and washed twice with aqueous sodium bicarbonate, once with water, once with brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by chromatography on silica gel using 3:97 acetone:hexanes as eluant to give 3.5 g of the title compound (25%). 1H NMR (500 MHz, CDCl3) δ 8.36 (s, 1H), 8.01 (d, 2H), 7.49 (m, 3H), 2.61 (s, 1H).

1. customThe volatiles were evaporated under reduced pressure
2. dissolutionThe residue was dissolved in ethanol (40 ml)
3. stirringthe mixture was stirred at room temperature for 3.5 hours
4. washwashed twice with aqueous sodium bicarbonate, once with water, once with brine
5. dry with materialdried over sodium sulfate
6. customThe solvent was evaporated under reduced pressure
7. customthe residue was purified by chromatography on silica gel using 3:97 acetone

ORD record

ord-1198b423266e4a08bff12cebeb83796b

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06608087B1