1,2-Dichlorobenzene → N-(2-chloro-4-nitrophenyl)-3-trifluoromethylbenzenesulfonamide

HRID 232159

Reaktionsgleichung

Reaktionsgleichung von HRID 232159
ClC1C=CC=CC=1Cl.[Cl:9][C:10]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:11]=1[NH2:12].[F:20][C:21]([F:33])([F:32])[C:22]1[CH:23]=[C:24]([S:28](Cl)(=[O:30])=[O:29])[CH:25]=[CH:26][CH:27]=1>N1C=CC=CC=1>[Cl:9][C:10]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:11]=1[NH:12][S:28]([C:24]1[CH:25]=[CH:26][CH:27]=[C:22]([C:21]([F:20])([F:32])[F:33])[CH:23]=1)(=[O:30])=[O:29]

Komponenten

5

Edukt 3

HCID 72391,2-DichlorobenzeneHCID 84922-Chloro-4-nitroanilineHCID 27332503-(Trifluoromethyl)benzenesulfonyl chloride

Produkt 1

HCID 13799089N-(2-chloro-4-nitrophenyl)-3-trifluoromethylbenzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

In a 400 ml flask, 200 ml of o-dichlorobenzene, 1 ml of pyridine and 1.7 g (0.01 mole) of 2-chloro-4-nitroaniline were charged. While stirring the contents at room temperature, 2.5 g (0.01 mole) of 3-trifluoromethylbenzenesulfonylchloride was added gradually over 30 minutes. Thereafter, the reaction mixture was heated and stirred for 8 hours under reflux (175°-180° C.) to complete the reaction. After cooling the reaction mixture to room temperature, it was thoroughly washed first with dilute hydrochloric acid and then with water. Subsequent to its dehydration with sodium sulfate, o-dichlorobenzene was distilled off under reduced pressure. The residue was subjected to silica gel chromatography (eluent: benzene) to isolate the intended Compound 1. m.p. 126°-127° C., yield 1.9 g (50%).

Aufarbeitung

  1. temperatureThereafter, the reaction mixture was heated
  2. stirringstirred for 8 hours
  3. temperatureunder reflux (175°-180° C.)
  4. customthe reaction
  5. temperatureAfter cooling the reaction mixture to room temperature
  6. washit was thoroughly washed first with dilute hydrochloric acid
  7. distillationSubsequent to its dehydration with sodium sulfate, o-dichlorobenzene was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-16d81bc93b0d4caa95a444a199096040
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04851445

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