Benzoyl chloride → N-(4-nitrostyrylsulfonyl)benzamide

HRID 972300Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 972300
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([CH:8]=[CH:9][S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.P(Cl)(Cl)(Cl)=O>C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:8]=[CH:9][S:10]([NH:13][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:11])=[O:12])=[CH:14][CH:15]=1)([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 7412Benzoyl chlorideHCID 24813Phosphorus oxychlorideHCID 536331802-(4-Nitrophenyl)ethene-1-sulfonamide

Produkt 1

HCID 54406439N-(4-nitrostyrylsulfonyl)benzamideAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 4-nitrostyrylsulfonamide (18.2 g., 0.08 mole), benzoyl chloride (12.6 g., 0.09 mole) and phosphorus oxychloride (13.8 g., 0.09 mole) is heated at steam bath temperature for 105 hr. The reaction mixture diluted with 20 ml. of ethyl acetate, cooled and filtered affords 19.0 g. (76% yield) of N-(4-nitrostyrylsulfonyl)benzamide, m.p. 192°-195° C., from ethyl acetate-hexane.

Aufarbeitung

  1. temperatureis heated at steam bath temperature for 105 hr
  2. additionThe reaction mixture diluted with 20 ml
  3. filtrationfiltered
  4. customaffords 19.0 g

Quellen und Nachweise

ORD-Eintrag
ord-31e1cb9f2454463bb4c05d683ba4c096
Quelldatensatz
uspto-grants-1977_10
Patentnummer
US04052455

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