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

HRID 1585059ノート

反応式

HRID 1585059 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].Cl.[F:19][C:20]([F:29])([F:28])[C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:15][C:14]1[N:25]([C:24]2[CH:26]=[CH:27][C:21]([C:20]([F:19])([F:28])[F:29])=[CH:22][CH:23]=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 27239614-(Trifluoromethyl)anilinium chlorideHCID 105388711-[4-(Methylsulfonyl)phenyl]-1,4-pentanedione

生成物 1

HCID 106197032-methyl-5-[4-(methylsulfonyl)phenyl]-1-[4-(trifluoromethyl)phenyl]-1H-pyrrole収率 78.4%

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), 4-(trifluoromethyl)aniline hydrochloride (257 mg, 1.3 mmol) and p-toluenesulfonic acid (30 mg) in toluene (80 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-5-[4-(methylsulfonyl)phenyl]-1-[4-(trifluoromethyl)phenyl]-1H-pyrrole (351 mg, 78%) as a white solid: mp (DSC) 130° C. Anal Calc'd. for C19H16NSO2F3 : C, 60.15; H, 4.25; N, 3.69. Found: C, 60.38; H, 4.44; N, 3.67.

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 solid (560 mg) was purified by chromatography (silica gel, hexane/ethyl acetate, 7/3)

出典と根拠

ORDレコード
ord-804254528d6a4f26a6103a886b108f0b
出典データセット
uspto-grants-1999_08
特許番号
US05935990

反応ノート

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