p-Toluenesulfinic acid → N-Pentylaniline

HRID 53864

Reaction equation

HRID 53864 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

HCID 75865N-PentylanilineYield 93%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-62cf0fb6663f4868a209d66bb418aa72
Source dataset
uspto-grants-1997_04
Patent number
US05621084

Linked notes

Loading…