Water → p-Toluenesulfonamide, N-benzyl-

HRID 1941463

Reaktionsgleichung

Reaktionsgleichung von HRID 1941463
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1.O>N1C=CC=CC=1>[CH2:1]([NH:8][S:15]([C:12]1[CH:13]=[CH:14][C:9]([CH3:19])=[CH:10][CH:11]=1)(=[O:17])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 7504Benzylamine

Produkt 1

HCID 95801p-Toluenesulfonamide, N-benzyl-Ausbeute 899,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of benzylamine (5 g, 4.67 mmol) in pyridine (25 ml) was added (cautiously) p-toluenesulphonyl chloride (10 g, 5.25 mmol). The deep red coloured solution was stirred at room temperature for 1 hour before being poured into water (80-100 ml). The oily precipitate which solidified on scratching was filtered and recrystallised from ethanol to give the title compound (10.98 g, 90% yield, m.p. 115°-116° C., (Lit.1 114° C.)). δH (CDCl3): 7.80(2H,m); 7.25(7H,m); 4.95(1H,t); 4.05(2H,d); 2.35(3H,s)ppm.

Aufarbeitung

  1. filtrationon scratching was filtered
  2. customrecrystallised from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-14713593dafd4e71b1f944704d0902c5
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05703246

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