4-Toluenesulfonyl chloride → 1-Tosyl-1H-indole-4-carbonitrile

HRID 41546

反応式

HRID 41546 の反応式
[C:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]2)#[N:2].C(N(C(C)C)CC)(C)C.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>C(#N)C>[S:27]([N:7]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:3]([C:1]#[N:2])[C:4]=2[CH:5]=[CH:6]1)([C:24]1[CH:25]=[CH:26][C:21]([CH3:31])=[CH:22][CH:23]=1)(=[O:29])=[O:28]

参加物

5

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 38176024-Cyanoindole

生成物 1

HCID 137163751-Tosyl-1H-indole-4-carbonitrile収率 91.6%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a stirred solution of 4-Cyano indole (0.5 g, 3.5 mmol), diisopropylethylamine (1.8 mL, 10.5 mmol) in acetonitrile (5.0 mL), p-toluene sulfonyl chloride (0.8 g, 4.22 mmol) was added and the mixture was stirred at rt for 4 h. The solvent was evaporated under reduced pressure and the residue was diluted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated to yield the title compound as brown colored solid (0.95 g, 90%). [1H-NMR (CDCl3, 300 MHz): δ 8.22 (d, 1H), 7.81-7.72 (m, 3H), 7.56 (d, 1H), 7.38 (t, 1H), 7.29-7.22 (m, 2H), 6.88 (d, 1H), 2.39 (s, 3H)].

後処理

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-f6a8372f5ae74f2bb80a712adca48919
出典データセット
uspto-grants-2013_09
特許番号
US08530648B2

関連ノート

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