Water → N-(4-Chloro-2-nitrophenyl)benzenesulfonamide

HRID 1279599

Reaktionsgleichung

Reaktionsgleichung von HRID 1279599
[N+:1]([C:4]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].N1C=CC=CC=1.[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>C(Cl)Cl>[C:18]1([S:24]([NH:6][C:5]2[CH:7]=[CH:8][C:9]([Cl:11])=[CH:10][C:4]=2[N+:1]([O-:3])=[O:2])(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 69794-Chloro-2-nitroanilineHCID 7369Benzenesulfonyl chloride

Produkt 1

HCID 555628N-(4-Chloro-2-nitrophenyl)benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-nitro-4-chloroaniline (500 mg) and pyridine (2.1 ml in methylene chloride (10 ml), benzenesulfonylchloride (1.2 ml) was added dropwise at 0° C. under an atmosphere of argon. The reaction mixture was stirred for 3 days at room temperature. To the reaction mixture, water was added. The mixture was extracted with ethyl acetate. The organic layer was washed, dried over and concentrated under the reduced pressure. The reside was recrystallized from AcOEt-hexane mixture solvent to give the by-product. The mother liquor was concentrated under the reduced pressure. The residue was purified on silica gel column chromatography (AcOEt-hexane) and recrystallized from AcOEt-hexane mixture solvent to give the title compound (175 mg) having the following physical data.

Aufarbeitung

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed
  3. customdried over and
  4. concentrationconcentrated under the reduced pressure
  5. customThe reside was recrystallized from AcOEt-hexane mixture solvent
  6. customto give the by-product
  7. concentrationThe mother liquor was concentrated under the reduced pressure
  8. customThe residue was purified on silica gel column chromatography (AcOEt-hexane)
  9. customrecrystallized from AcOEt-hexane mixture solvent

Quellen und Nachweise

ORD-Eintrag
ord-233de6277ac44ef7b0f02fea12d39e9c
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06448290B1

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