反応 #58915

反応方程式

2-(4-nitrophenyl)ethanethioamide

ethyl bromopyruvate

→

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

溶媒

ethanol

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度under reflux for 30 min
3. 3
   濃縮The reaction mixture was concentrated
4. 4
   workup.ADDITIONethyl acetate was added to the residue
5. 5
   洗浄The mixture was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
6. 6
   乾燥dried over anhydrous magnesium sulfate
7. 7
   濃縮concentrated

実験手順

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.

出典