Chloroacetaldehyde → 2-[2-(4-Nitrophenyl)ethyl]-1,3-thiazole

HRID 30652

반응식

HRID 30652 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12](=[S:14])[NH2:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[CH2:16][CH:17]=O>C(O)(C)(C)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][C:12]2[S:14][CH:16]=[CH:17][N:13]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

참가 물질

4

반응물 2

HCID 33ChloroacetaldehydeHCID 826731463-(4-Nitrophenyl)propanethioamide

생성물 1

HCID 692092882-[2-(4-Nitrophenyl)ethyl]-1,3-thiazole수율 28%

시약·촉매·용매 1

HCID 6386tert-Butanol용매

실험 절차

A mixture of 3-(4-nitrophenyl)propanethioamide (1.0 g), chloroacetaldehyde (40% aqueous solution, 2.83 g) and tert-butanol (20 mL) was heated under reflux for 2 hrs. The reaction mixture was concentrated, and saturated aqueous sodium hydrogen carbonate was 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 2-[2-(4-nitrophenyl)ethyl]-1,3-thiazole as pale-yellow crystals (0.31 g, yield 28%) from a fraction eluted with hexane-ethyl acetate (3:1, v/v). Recrystallization thereof from ethyl acetate-hexane gave pale-yellow prism crystals. melting point: 92-93° C.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hrs
  3. concentrationThe reaction mixture was concentrated
  4. additionsaturated aqueous sodium hydrogen carbonate was 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-4645e2f336fb42c1ac43af807b1a0cc1
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423159B2

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