Ethyl 2-chloroacetoacetate → HCID 23560694, compound

A solution of 2-methylpropanethioamide (3.1 g, 30 mmol) and ethyl 2-chloroacetoacetate (3.29 g, 20 mmol) in ethanol (40 mL) was heated at reflux for 3 h. The reaction mixture was evaporated to dryness and the residue was taken up in dichloromethane (50 mL) and the solution was washed with saturated sodium bicarbonate solution (2×25 mL). The aqueous layers were back-washed with dichloromethane (25 mL), then the combined dichloromethane layers were dried (MgSO4), filtered and concentrated under vacuum. The residue was purified using a Waters Prep 500 apparatus (silica gel dual column; 10% ethyl acetate/hexanes). Evaporation of the appropriate fractions afforded 2-(1-methylethyl)-4-methylthiazole-5-carboxylic acid ethyl ester (4.0 g, 93% yield).

1. temperatureat reflux for 3 h
2. customThe reaction mixture was evaporated to dryness
3. washthe solution was washed with saturated sodium bicarbonate solution (2×25 mL)
4. washThe aqueous layers were back-washed with dichloromethane (25 mL)
5. dry with materialthe combined dichloromethane layers were dried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated under vacuum
8. customThe residue was purified
9. customEvaporation of the appropriate fractions

ORD record

ord-fd7d07f052e4437d96ec6f97e21d2f6f

Source dataset

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06515124B2