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

HRID 41546노트

반응식

HRID 41546 반응식
[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]

참가 물질

5

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 38176024-Cyanoindole

생성물 1

HCID 137163751-Tosyl-1H-indole-4-carbonitrile수율 91.6%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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)].

후처리

  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

출처 및 근거

ORD 기록
ord-f6a8372f5ae74f2bb80a712adca48919
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530648B2

반응 노트

불러오는 중…