Reacción #58915

Ecuación de reacción

2-(4-nitrophenyl)ethanethioamide

ethyl bromopyruvate

→

ethyl 2-(4-nitrobenzyl)-1,3-thiazole-4-carboxylate

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturaunder reflux for 30 min
3. 3
   ConcentraciónThe reaction mixture was concentrated
4. 4
   workup.ADDITIONethyl acetate was added to the residue
5. 5
   LavadoThe mixture was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
6. 6
   Secadodried over anhydrous magnesium sulfate
7. 7
   Concentraciónconcentrated

Procedimiento

A mixture of 2-(4-nitrophenyl)ethanethioamide (1.50 g), ethyl bromopyruvate (1.64 g) and ethanol (50 mL) was heated under reflux for 30 min. The reaction mixture was concentrated, and ethyl acetate was added to the residue. The mixture was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and ethyl 2-(4-nitrobenzyl)-1,3-thiazole-4-carboxylate was obtained as pale-yellow crystals (1.79 g, yield 81%) from a fraction eluted with hexane-ethyl acetate (1:1, v/v). Recrystallization thereof from ethyl acetate-hexane gave pale-yellow prism crystals. melting point: 122-123° C.

Fuente