Hydrochloric Acid → N1-(4-methoxybenzoyl)-N2-(2-naphthoyl)-benzenediamine

HRID 395701

Reaktionsgleichung

Reaktionsgleichung von HRID 395701
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([C:7]([NH:9][C:10]2[C:11]([NH2:16])=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:8])=[CH:5][CH:4]=1.N1C=CC=CC=1.[CH:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][C:26]=1[C:35](Cl)=[O:36].Cl>C(Cl)(Cl)Cl.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C:10]2[C:11]([NH:16][C:35]([C:26]3[CH:27]=[CH:28][C:29]4[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:25]=3)=[O:36])=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:8])=[CH:17][CH:18]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 752462-Naphthoyl chlorideHCID 785232N-(2-Aminophenyl)-4-methoxybenzamide

Produkt 1

HCID 21352792N1-(4-methoxybenzoyl)-N2-(2-naphthoyl)-benzenediamineAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of N1-(4-methoxybenzoyl)-1,2-benzenediamine (200 mg, 0.826 mmol) and pyridine (0.25 mL) in chloroform (5 mL) was treated with 2-naphthoyl chloride (158 mg, 0.826 mmol). After 20 h, the mixture was poured into a mixture of ethyl acetate and 1 N aqueous hydrochloric acid. The organic layer was washed with water, saturated sodium chloride solution, and dried (potassium carbonate), filtered, and concentrated in vacuo. Recrystallization from hexanes/ethyl acetate yielded 211 mg (65%) of the title compound.

Aufarbeitung

  1. washThe organic layer was washed with water, saturated sodium chloride solution
  2. dry with materialdried (potassium carbonate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customRecrystallization from hexanes/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-610667b255af48dfb5d730a62b4d12e7
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06605626B2

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