Aklomide → 2-Chloro-4-nitrobenzonitrile

HRID 2295371

Reaktionsgleichung

Reaktionsgleichung von HRID 2295371
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:7]=1[C:8]([NH2:10])=O>C1C=CC=CC=1>[Cl:5][C:6]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:7]=1[C:8]#[N:10]

Komponenten

4

Edukt 2

HCID 2075AklomideHCID 24386Thionyl Chloride

Produkt 1

HCID 1414012-Chloro-4-nitrobenzonitrileAusbeute 79,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

Thionyl chloride (1,000 g, 8.4 m) was then added to the 2-chloro-4-nitrobenzamide (200 g, 1 m) while the mixture was warmed. After addition, the mixture was refluxed for approximately three hours. The excess thionyl chloride was removed by distillation leaving a reaction mixture residue. Benzene (500 ml) was added to the cold reaction mixture residue to extract the reaction product. The extract was washed with diluted sodium hydroxide solution and water until neutralized and then dried over anhydrous sodium sulfate. The benzene solvent was distilled off and the reaction product was crystallized from methanol to yield 2-chloro-4-nitrobenzonitrile (145 g, 79%, mp 73°-75° C.).

Aufarbeitung

  1. temperaturewas warmed
  2. additionAfter addition
  3. temperaturethe mixture was refluxed for approximately three hours
  4. customThe excess thionyl chloride was removed by distillation
  5. customleaving a reaction mixture residue
  6. extractionto extract the reaction product
  7. washThe extract was washed with diluted sodium hydroxide solution and water until neutralized and
  8. dry with materialthen dried over anhydrous sodium sulfate
  9. distillationThe benzene solvent was distilled off
  10. customthe reaction product was crystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-908ac15f209d4eec953a0050b68fc201
Quelldatensatz
uspto-grants-1984_01
Patentnummer
US04424371

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