p-Toluenesulfonic acid → 2-Methyl-1-(4-methylphenyl)-5-(4-methylsulfonylphenyl)pyrrole

HRID 1585060노트

반응식

HRID 1585060 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][C:22]([CH3:25])=[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][C:22]([CH3:25])=[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 7813p-ToluidineHCID 105388711-[4-(Methylsulfonyl)phenyl]-1,4-pentanedione

생성물 1

HCID 106638332-Methyl-1-(4-methylphenyl)-5-(4-methylsulfonylphenyl)pyrrole수율 91%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of 1-(4-methylsulfonylphenyl)-1,4-pentanedione (Example 1, Step 2) (335 mg, 1.32 mmol), p-toluidine (156 mg, 1.45 mmol) and p-toluenesulfonic acid (25 mg) in toluene (100 ml) was heated to reflux for 20 hours. The reaction mixture was cooled, filtered and concentrated. The crude solid (560 mg) was purified by chromatography (silica gel, hexane/ethyl acetate, 7/3) to give 2-methyl-1-(4-methylphenyl)-5-[4-(methylsulfonyl)phenyl]-1H-pyrrole (390 mg, 91%) as a white solid: mp (DSC) 144° C. Anal Calc'd. for C19H19NSO2 : C, 70.13; H, 5.88; N, 4.30; S, 9.85. Found: C, 69.99; H, 6.23; N, 4.18; S, 9.74.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 20 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude solid (560 mg) was purified by chromatography (silica gel, hexane/ethyl acetate, 7/3)

출처 및 근거

ORD 기록
ord-8476c49c44d641a4a4275ba1682cd920
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05935990

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