Benzenesulfonyl chloride → 2'-Chloro-4'-nitrobenzenesulfonanilide

HRID 399477

Reaktionsgleichung

Reaktionsgleichung von HRID 399477
[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[C:12]1([S:18](Cl)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH:4][S:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:20])=[O:19]

Komponenten

4

Edukt 2

HCID 7369Benzenesulfonyl chlorideHCID 84922-Chloro-4-nitroaniline

Produkt 1

HCID 2318362'-Chloro-4'-nitrobenzenesulfonanilide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 2-chloro-4-nitroaniline (4.33 g), benzenesulphonyl chloride (3.25 ml) and pyridine (2.5 ml) was stirred and heated to 100° C. for 18 hours. The mixture was cooled to ambient temperature and partitioned between methylene chloride and 2M aqueous hydrochloric acid. The organic phase was washed with water, dried and evaporated. The residue was recrystallised from ethyl acetate to give N-(2-chloro-4-nitrophenyl)benzenesulphonamide (6.07 g), m.p. 155°-157° C.

Aufarbeitung

  1. temperatureThe mixture was cooled to ambient temperature
  2. custompartitioned between methylene chloride and 2M aqueous hydrochloric acid
  3. washThe organic phase was washed with water
  4. customdried
  5. customevaporated
  6. customThe residue was recrystallised from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c466971758344711aafc5413143c01f3
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05821246

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