p-Toluenesulfonic acid → 1-Phenyl-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrole

HRID 1585057노트

반응식

HRID 1585057 반응식
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=O)[CH2:12][CH2:13][C:14](=O)[CH3:15])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:15][C:14]1[N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:11]([C:8]2[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=2)=[CH:12][CH:13]=1

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 6115AnilineHCID 105388711-[4-(Methylsulfonyl)phenyl]-1,4-pentanedione

생성물 1

HCID 108050031-Phenyl-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrole수율 83%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of 1-(4-methylsulfonylphenyl)-1,4-pentanedione (Example 1, step 2) (300 mg, 1.18 mmol), aniline (0.12 ml, 1.3 mmol) and p-toluenesulfonic acid (25 mg) in toluene (50 ml) was heated to reflux for 20 hours. The reaction mixture was cooled, filtered and concentrated. The crude brownish solid (420 mg) was purified by chromatography (silica gel, hexane/ethyl acetate, 7/3) to give 2-methyl-5-[4-(methylsulfonyl)phenyl]-1-phenyl-1H-pyrrole (305 mg, 83%) as a white solid: mp (DSC) 148° C. Anal Calc'd. for C18H17NSO2 : C, 69.43; H, 5.50; N, 4.50; S, 10.30. Found: C, 69.18; H, 5.42; N, 4.42; S, 10.06.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 20 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude brownish solid (420 mg) was purified by chromatography (silica gel, hexane/ethyl acetate, 7/3)

출처 및 근거

ORD 기록
ord-8f56d9c5a2ad412f86694c26b856ea36
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05935990

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