Acetyl chloride → 1-[1-(4-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrol-3-yl]ethanone

HRID 1585075노트

반응식

HRID 1585075 반응식
[C:1](Cl)(=[O:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[F:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=3)=[CH:19][CH:18]=[C:17]2[CH3:31])=[CH:12][CH:11]=1>C(Cl)Cl>[F:9][C:10]1[CH:11]=[CH:12][C:13]([N:16]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=3)=[CH:19][C:18]([C:1](=[O:3])[CH3:2])=[C:17]2[CH3:31])=[CH:14][CH:15]=1

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 27657241-(4-Fluorophenyl)-2-methyl-5-(4-methylsulfonylphenyl)pyrroleHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 105232551-[1-(4-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrol-3-yl]ethanone수율 30.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Acetyl chloride (120 41, 1.67 mmol) was slowly added to a stirred slurry of aluminum chloride (223 mg, 1.67 mmol) in methylene chloride (15 ml) at -5° C. After 30 minutes, a solution 1-(4-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl)-1H-pyrrole (Example 1) (500 mg, 1.52 mmol) in methylene chloride (20 ml) was added. The reaction mixture was warmed to room temperature and stirred for 18 hours. The reaction mixture was poured over ice-water and extracted with methylene chloride. The organic fraction was washed with brine, dried (MgSO4), filtered and concentrated. The crude yellowish solid (570 mg) was purified by chromatography (silica gel, hexane/ethyl acetate, 6/4) to give 1-[1-(4-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrol-3-yl]ethanone (170 mg, 30%) as a white solid: mp (DSC) 211° C. Anal Calc'd. for C20H18NSFO3 ·0.25 H2O: C, 63.90; H, 4.96; N, 3.75. Found: C, 63.96; H, 5.04; N, 3.65.

후처리

  1. extractionextracted with methylene chloride
  2. washThe organic fraction was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude yellowish solid (570 mg) was purified by chromatography (silica gel, hexane/ethyl acetate, 6/4)

출처 및 근거

ORD 기록
ord-40b8a59bb14c405a9c6d53b3f15c3190
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05935990

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