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

HRID 1585057ノート

反応式

HRID 1585057 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-8f56d9c5a2ad412f86694c26b856ea36
出典データセット
uspto-grants-1999_08
特許番号
US05935990

反応ノート

読み込み中…