Benzoyl chloride → N-benzoyl-5-methylindole

HRID 1886454

반응식

HRID 1886454 반응식
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.C(N(CC)CC)C.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl>[C:18]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([CH3:1])=[CH:10][CH:9]=2)[CH:5]=[CH:6]1)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

5

반응물 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 119785-Methylindole

생성물 1

HCID 10354051N-benzoyl-5-methylindole

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 5-methylindole (1.0 g, 7.6 mmol) in 8.0 mL of CH2Cl2 was added N,N-dimethylamino pyridine (0.186 g, 1.52 mmol), 2.12 mL (15.24 mmol) of triethylamine and 0.97 mL (1.18 g, 8.39 mmol) of benzoyl chloride. The resulting solution was stirred for 16 hours at room temperature. The solution was diluted with 500 mL of CH2Cl2 and washed with 200 mL of saturated aqueous NaHCO3 and 200 mL of brine. The organic phase was dried over MgSO4, filtered, and concentrated to a yellow oil. The resultant oil was flash chromatographed eluting with 20% ethyl acetate in hexane yielding 1.73 g (96%) of the titled compound as a white powder.

후처리

  1. washwashed with 200 mL of saturated aqueous NaHCO3 and 200 mL of brine
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to a yellow oil
  5. customchromatographed
  6. washeluting with 20% ethyl acetate in hexane yielding 1.73 g (96%) of the titled compound as a white powder

출처 및 근거

ORD 기록
ord-295f6a6f0af145a79198105883f7c12c
출처 데이터셋
uspto-grants-1992_09
특허 번호
US05151435

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