3-Chloro-2-butanone → 4,5-Dimethyl-2-(4-nitrobenzyl)-1,3-thiazole

HRID 30671

反応式

HRID 30671 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](=[S:13])[NH2:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[CH:15]([C:17](=O)[CH3:18])[CH3:16]>C(O)(C)(C)C>[CH3:16][C:15]1[N:12]=[C:11]([CH2:10][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[S:13][C:17]=1[CH3:18]

参加物

4

反応物 2

HCID 200263-Chloro-2-butanoneHCID 27773372-(4-Nitrophenyl)thioacetamide

生成物 1

HCID 692093994,5-Dimethyl-2-(4-nitrobenzyl)-1,3-thiazole収率 47.7%

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

A mixture of 2-(4-nitrophenyl)ethanethioamide (1.11 g), 2-chloro-3-butanone (0.75 g) and tert-butanol (50 ml) was heated under reflux for 4 days. The reaction mixture was concentrated, and water and saturated aqueous sodium hydrogen carbonate were added to the residue. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 4,5-dimethyl-2-(4-nitrobenzyl)-1,3-thiazole as pale-yellow crystals (0.67 g, yield 47%) from a fraction eluted with hexane-ethyl acetate (2:1-1:1, v/v). Recrystallization thereof from ethyl acetate-hexane gave pale-yellow prism crystals. melting point: 93-94° C.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 4 days
  3. concentrationThe reaction mixture was concentrated
  4. additionwater and saturated aqueous sodium hydrogen carbonate were added to the residue
  5. extractionThe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-ead65ccebab24233a2bd57f0d894e914
出典データセット
uspto-grants-2008_09
特許番号
US07423159B2

関連ノート

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