p-Toluenesulfinic acid → N-Pentylaniline

HRID 53864

반응식

HRID 53864 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

HCID 75865N-Pentylaniline수율 93%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-62cf0fb6663f4868a209d66bb418aa72
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05621084

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