p-Toluenesulfinic acid → N-Pentylaniline

HRID 53864Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 53864
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]

Komponenten

6

Edukt 3

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

Produkt 1

HCID 75865N-PentylanilineAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-62cf0fb6663f4868a209d66bb418aa72
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05621084

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