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

HRID 30638

反応式

HRID 30638 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].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

参加物

4

反応物 2

HCID 11715BromoacetoneHCID 27773372-(4-Nitrophenyl)thioacetamide

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6e90ae0f47444898ac20281d8b2f1b85
出典データセット
uspto-grants-2008_09
特許番号
US07423159B2

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