4-Methylbenzoyl Chloride → 1-(1-Benzenesulfonyl-1H-pyrrol-3-yl)-1-p-tolyl-methanone

HRID 31541

反応式

HRID 31541 の反応式
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1([CH3:14])[CH:10]=[CH:9][C:8]([C:11](Cl)=[O:12])=[CH:7][CH:6]=1.[C:15]1([S:21]([N:24]2[CH:28]=[CH:27][CH:26]=[CH:25]2)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)CCl>[C:15]1([S:21]([N:24]2[CH:25]=[CH:26][C:27]([C:11]([C:8]3[CH:9]=[CH:10][C:5]([CH3:14])=[CH:6][CH:7]=3)=[O:12])=[CH:28]2)(=[O:23])=[O:22])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

参加物

5

反応物 3

HCID 134054-Methylbenzoyl ChlorideHCID 1401461-PhenylsulfonylpyrroleHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 4756391-(1-Benzenesulfonyl-1H-pyrrol-3-yl)-1-p-tolyl-methanone収率 105.3%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒3 回

実験手順

Under nitrogen atmosphere, to a suspension of aluminum chloride (4.62 g, 34.7 mmol) in ethylene chloride (50 mL) was added a solution of p-toluoyl chloride (4.91 g, 31.8 mmol) in ethylene chloride (5 mL) at room temperature over a period of 10 minutes. The mixture was stirred for 30 minutes, and thereto was added a solution of 1-benzenesulfonyl-1H-pyrrole (6.00 g, 28.9 mmol) in ethylene chloride (10 mL) over a period of 10 minutes. The mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into ice-water, and the aqueous layer was extracted twice with dichloromethane. The organic layers were combined, dried, and filtered. The filtrate was concentrated, and the residue was purified by silica gel column chromatography to give the title compound (9.9 g, 100%).

後処理

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. extractionthe aqueous layer was extracted twice with dichloromethane
  3. customdried
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-ba8804115d7f438d8e16948d3df34747
出典データセット
uspto-grants-2008_09
特許番号
US07425642B2

関連ノート

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