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

HRID 30671

반응식

HRID 30671 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6386tert-Butanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ead65ccebab24233a2bd57f0d894e914
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423159B2

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