2-Chlorocyclohexanone → 2-(4-Nitrobenzyl)-4,5,6,7-tetrahydro-1,3-benzothiazole

HRID 30672

反応式

HRID 30672 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]1[CH2:20][CH2:19][CH2:18][CH2:17][C:16]1=O>C(O)(C)(C)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]2[S:13][C:15]3[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=3[N:12]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

参加物

4

反応物 2

HCID 132032-ChlorocyclohexanoneHCID 27773372-(4-Nitrophenyl)thioacetamide

生成物 1

HCID 692104872-(4-Nitrobenzyl)-4,5,6,7-tetrahydro-1,3-benzothiazole収率 67.2%

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

A mixture of 2-(4-nitrophenyl)ethanethioamide (7.0 g), 2-chloro-cyclohexanone (7.28 g) and tert-butanol (100 mL) was heated under reflux for 3 days. 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-(4-nitrobenzyl)-4,5,6,7-tetrahydro-1,3-benzothiazole as pale-brown crystals (6.58 g, yield 66%) 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: 118-119° C.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 3 days
  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-8b03f05fd29e49cf9652f8e47b47672e
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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