Methyl p-toluenesulfonate → 2-bromo-4-(N-methylacetamido)thiazole

HRID 26204ノート

反応式

HRID 26204 の反応式
[C:1]([NH:4][C:5]1[N:6]=[C:7]([Br:10])[S:8][CH:9]=1)(=[O:3])[CH3:2].S(C1C=CC(C)=CC=1)(O[CH3:15])(=O)=O.[H-].[Na+]>C(#N)C>[Br:10][C:7]1[S:8][CH:9]=[C:5]([N:4]([CH3:15])[C:1](=[O:3])[CH3:2])[N:6]=1

参加物

5

反応物 3

HCID 6645Methyl p-toluenesulfonateHCID 24758Sodium hydrideHCID 202940434-Acetamido-2-bromo-thiazole

生成物 1

HCID 203771682-bromo-4-(N-methylacetamido)thiazole収率 32%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

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%).

後処理

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate evaporated under reduced pressure
  3. customThe residue was chromatographed on silica (Woelm grade, 1, 150 g)
  4. customEvaporation of the appropriate fractions
  5. customfollowed by recrystallisation from hexane

出典と根拠

ORDレコード
ord-b77032338537498ca06597cc4eb4f8a0
出典データセット
uspto-grants-1979_04
特許番号
US04148904

反応ノート

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