Benzenesulfonyl chloride → 1-(Phenylsulfonyl)-3-indolecarboxaldehyde

HRID 522589

반응식

HRID 522589 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[O:11])=[CH:2]1.[OH-].[K+].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[C:14]1([S:20]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]([CH:10]=[O:11])=[CH:2]2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

5

반응물 3

HCID 7369Benzenesulfonyl chlorideHCID 10256Indole-3-CarboxaldehydeHCID 14797Potassium Hydroxide

생성물 1

HCID 3633341-(Phenylsulfonyl)-3-indolecarboxaldehyde수율 33%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of indole 3-carboxaldehyde (8y) (100 mmol) in ethanol (500 mL) at RT was added potassium hydroxide (1.1 equiv). The mixture was stirred until total solubilization. The ethanol was completely removed in vacuum and the residual was dissolved in acetone (250 mL) followed by adding benzenesulfonyl chloride (1.1 equiv, 110 mmol). The reaction mixture was stirred for half hour. The precipitate was filtered off and the filtrate was concentrated and recrystallized from methanol to give a white solid. Yield: 33%. 1H NMR (500 MHz, CDCl3) δ 10.17 (s, 1H), 8.25-8.39 (m, 2H), 7.97-8.09 (m, 3H), 7.69 (t, J=7.33 Hz, 1H), 7.59 (t, J=7.5 Hz, 2H), 7.39-7.54 (m, 2H). MS (ESI) calcd for C15H11NO3S 285.1. Found 286.0 [M+H]+.

후처리

  1. customThe ethanol was completely removed in vacuum
  2. dissolutionthe residual was dissolved in acetone (250 mL)
  3. stirringThe reaction mixture was stirred for half hour
  4. filtrationThe precipitate was filtered off
  5. concentrationthe filtrate was concentrated
  6. customrecrystallized from methanol
  7. customto give a white solid

출처 및 근거

ORD 기록
ord-b3baf7e1a78044428172788db1013774
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334242B2

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