Bromoacetone → 4-Methyl-2-(4-nitrobenzyl)-1,3-thiazole

HRID 30638

반응식

HRID 30638 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].Br[CH2:15][C:16](=O)[CH3:17]>C(O)C>[CH3:17][C:16]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][CH:15]=1

참가 물질

4

반응물 2

HCID 11715BromoacetoneHCID 27773372-(4-Nitrophenyl)thioacetamide

생성물 1

HCID 692091384-Methyl-2-(4-nitrobenzyl)-1,3-thiazole

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 2-(4-nitrophenyl)ethanethioamide (0.50 g), 1-bromo-2-propanone (0.43 g) and ethanol (20 mL) was heated under reflux for 1 hr. 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, and 4-methyl-2-(4-nitrobenzyl)-1,3-thiazole was obtained as pale-yellow crystals (0.37 g, yield 63%) from a fraction eluted with hexane-ethyl acetate (2:1-1:1, v/v). Recrystallization thereof from ethyl acetate-hexane gave colorless prism crystals. melting point: 81-82° C.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hr
  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-6e90ae0f47444898ac20281d8b2f1b85
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423159B2

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