HCID 18918306, Verbindung → P-Toluenesulfonamide

HRID 1290473Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1290473
C(C1C=CC(C[NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=CC=1)(=O)C>C(OCC)(=O)C>[CH3:21][C:18]1[CH:17]=[CH:16][C:15]([S:12]([NH2:11])(=[O:14])=[O:13])=[CH:20][CH:19]=1

Komponenten

3

Edukt 1

HCID 18918306HCID 18918306, Verbindung

Produkt 1

HCID 6269P-Toluenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of the product of step i) (1.0 g) and cupric bromide (1.47 g) in ethyl acetate (3.0 ml) was heated at reflux temperature for 16 hours. Additional cupric bromide (1.0 g) was added and heating continued for a further 8 hours. The mixture was filtered and the filtrate concentrated to dryness in vacuo. This residue was purified by flash chromatography on silica, eluting with hexane/ethyl acetate (2:1 v/v). Evaporation of the fractions gave N-(14-bromoacetylphenyl]methyl)-4-methylphenylsulphonamide, 1.13 g, as a white solid: m.p. 116°-117° C., NMR (CDl3) δ 7.9(2H,d), 7.75(2H,d), 7.34(4H,m), 4.77(1H,t), 4.40(2H,s), 4.22(2H,d), 2.44(3H,s): m/e 382/384 (M+H)+, 1 Br pattern.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux temperature for 16 hours
  3. temperatureheating
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate concentrated to dryness in vacuo
  6. customThis residue was purified by flash chromatography on silica
  7. washeluting with hexane/ethyl acetate (2:1 v/v)
  8. customEvaporation of the fractions

Quellen und Nachweise

ORD-Eintrag
ord-ca186b1ddb5f4917b6e742dd36d80bb1
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05750754

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