反応 #54482

反応方程式

4-acetamido-2-bromothiazole

4-Acetamido-2-bromothiazole

methyl tosylate

sodium hydride

→

title compound

収率 32.0%

2-Bromo-4-(N-methylacetamido)thiazole

収率 32.0%

溶媒

—

oil

acetonitrile

反応条件

後処理

1. 1
   ろ過The reaction mixture was filtered
2. 2
   その他the filtrate evaporated under reduced pressure
3. 3
   その他The residue was chromatographed on silica (Woelm grade, 1, 150 g)
4. 4
   その他Evaporation of the appropriate fractions
5. 5
   その他followed by recrystallisation from hexane

実験手順

A solution of 4-acetamido-2-bromothiazole (prepared as described in Example 1) and methyl tosylate (4.65 g, 25 mM) in dry acetonitrile (125 ml) was treated with a 60% dispersion of sodium hydride in oil (1 g, 25 mM) and the mixture stirred 72 hours at ambient temperature. The reaction mixture was filtered and the filtrate evaporated under reduced pressure. The residue was chromatographed on silica (Woelm grade, 1, 150 g) using 2% methanol in chloroform as eluant. Evaporation of the appropriate fractions followed by recrystallisation from hexane gave the title compound (1.9 g, 32%) mp 84° C. Found: C, 30.55; H, 2.95; N, 11.8%. C6H7N2BrOS requires C, 30.7; H, 3.0; N, 11.9%).

出典