Benzenesulfonyl chloride → 1H-Indole, 5-nitro-1-(phenylsulfonyl)-

HRID 84199

반응식

HRID 84199 반응식
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].[OH-].[K+].[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[C:15]1([S:21]([N:9]2[C:10]3[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=3)[CH:7]=[CH:8]2)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

6

반응물 3

HCID 7369Benzenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 225235-Nitroindole

생성물 1

HCID 121633031H-Indole, 5-nitro-1-(phenylsulfonyl)-수율 92.2%

시약·촉매·용매 2

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 6344Dichloromethane용매

실험 절차

After a suspension of 5-nitroindole (25) (1.00 g, 6.17 mmol), tetrabutylammonium bisulfate (0.32 g, 0.93 mmol) and KOH (0.69 g, 12.33 mmol) in CH2Cl2 (20 mL) was stirred for 30 min, benzenesulfonyl chloride (1.18 ml, 9.25 mmol) was added and stirred at room temperature overnight. The reaction was quenched with water extracted with CH2Cl2 (20 mL×3). The combined organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure to give a yellow residue, which was purified by silica gel chromatography (EtOAc:n-hexane=1:4) to afford 26 (1.72 g). 1H NMR (500 MHz, CD3OD): δ 6.81 (d, J=3.6 Hz, 1H), 7.48-7.51 (m, 2H), 7.58-7.61 (m, 1H), 7.73 (d, J=3.69 Hz, 1H), 7.90 (d, J=7.64 Hz, 2H), 8.09 (d, J=9.0 Hz, 1H), 8.21 (dd, J=9.0, 2.0 Hz, 1H), 8.47 (d, J=2.0 Hz, 1H).

후처리

  1. stirringstirred at room temperature overnight
  2. customThe reaction was quenched with water
  3. extractionextracted with CH2Cl2 (20 mL×3)
  4. dry with materialThe combined organic layer was dried over anhydrous MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customto give a yellow residue, which
  7. customwas purified by silica gel chromatography (EtOAc:n-hexane=1:4)

출처 및 근거

ORD 기록
ord-9f906ee874db41029ec8559537c63833
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846748B2

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