4-Methylbenzoyl Chloride → (1-benzenesulfonyl-1H-pyrrol-2-yl)(4-methylphenyl)ketone

HRID 31540

反応式

HRID 31540 の反応式
[C:1]1([S:7]([N:10]2[CH:14]=[CH:13][CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15]1([CH3:24])[CH:20]=[CH:19][C:18]([C:21](Cl)=[O:22])=[CH:17][CH:16]=1>ClCCl>[CH3:24][C:15]1[CH:20]=[CH:19][C:18]([C:21]([C:14]2[N:10]([S:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)(=[O:9])=[O:8])[CH:11]=[CH:12][CH:13]=2)=[O:22])=[CH:17][CH:16]=1

参加物

4

反応物 2

HCID 134054-Methylbenzoyl ChlorideHCID 1401461-Phenylsulfonylpyrrole

生成物 1

HCID 22928710(1-benzenesulfonyl-1H-pyrrol-2-yl)(4-methylphenyl)ketone収率 71%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
10 °C

実験手順

Under nitrogen atmosphere, to a solution of 1-benzenesulfonyl-1H-pyrrole (284 g, 1.37 mol) in dichloromethane (1.0 L) were added p-toluoyl chloride (318 g, 2.06 mol) and boron trifluoride ether complex (350 g, 2.47 mol), and the mixture was allowed to stand at room temperature for 7 days. The reaction solution was washed successively with 1N aqueous hydrochloric acid solution (750 mL×2), 1N aqueous sodium hydroxide solution (750 mL) and saturated saline (100 mL), dried, and filtered. The filtrate was concentrated under atmospheric pressure until about 500 ml, and thereto was added hexane (500 mL). The reaction mixture was further concentrated until about 500 ml, cooled to 10° C., and the resulting crystals were collected by filtration. The obtained crystals were washed successively with hexane and toluene to give the title compound (315 g, 71%).

後処理

  1. washThe reaction solution was washed successively with 1N aqueous hydrochloric acid solution (750 mL×2), 1N aqueous sodium hydroxide solution (750 mL) and saturated saline (100 mL)
  2. customdried
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under atmospheric pressure until about 500 ml
  5. additionwas added hexane (500 mL)
  6. concentrationThe reaction mixture was further concentrated until about 500 ml
  7. filtrationthe resulting crystals were collected by filtration
  8. washThe obtained crystals were washed successively with hexane and toluene

出典と根拠

ORDレコード
ord-69e667da46634917ac0f063ee4dba93a
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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