p-Toluenesulfinic acid → N-Pentylaniline

HRID 53864

反応式

HRID 53864 の反応式
C1(C)C=CC(S(O)=O)=CC=1.C([N:14]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])C=C.C(=O)([O-])O.[Na+]>ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:15]([NH:14][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH2:16][CH2:17][CH2:18][CH3:19]

参加物

6

反応物 3

HCID 10818p-Toluenesulfinic acidHCID 516892Sodium BicarbonateHCID 10608235N-allyl-N-pentylphenylamine

生成物 1

HCID 75865N-Pentylaniline収率 93%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6344Dichloromethane溶媒

実験手順

p-Toluenesulfinic acid (188 ml, 1.20 mmol) was added at room temperature to a solution of N-allyl-N-pentylphenylamine(221 mg, 1.08 mmol) and tetrakis(triphenylphosphine)palladium(87.8 mg, 75.9 μmol) in dichloromethane(11 ml). The reaction mixture was stirred at room temperature for 60 minutes and saturated aqueous sodium hydrogen carbonate(6.8 ml) was added. After stirred for 5 minutes, the mixture was extracted with ether(80 ml). The extract was dried on magnesium sulfate, filterd and concentrated in vacuum. The residue was chromatographed on silica gel to give N-pentylphenylamine(164 mg) in 93% yield as a colorless oil.

後処理

  1. stirringAfter stirred for 5 minutes
  2. extractionthe mixture was extracted with ether(80 ml)
  3. customThe extract was dried on magnesium sulfate, filterd
  4. concentrationconcentrated in vacuum
  5. customThe residue was chromatographed on silica gel

出典と根拠

ORDレコード
ord-62cf0fb6663f4868a209d66bb418aa72
出典データセット
uspto-grants-1997_04
特許番号
US05621084

関連ノート

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