Dimethylformamide → 7-Chloro-5-phenyl-1,2,3,4-tetrahydro-2-nitromethylene-5H-1, 5-benzodiazepin-4-one

HRID 1679288Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1679288
CC(C)([O-])C.[K+].CN(C)C=O.[N+:12]([CH3:15])([O-:14])=[O:13].[Cl:16][C:17]1[CH:38]=[CH:37][C:20]2[N:21]=[C:22](NCN=O)[CH2:23][C:24](=[O:32])[N:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:19]=2[CH:18]=1>O.C(O)(=O)C>[Cl:16][C:17]1[CH:38]=[CH:37][C:20]2[NH:21][C:22](=[CH:15][N+:12]([O-:14])=[O:13])[CH2:23][C:24](=[O:32])[N:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:19]=2[CH:18]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 6375NitromethaneHCID 23665647Potassium tert-butoxideHCID 1785263748-chloro-4-(nitrosomethylamino)-1-phenyl-3H-1,5-benzodiazepin-2-one

Produkt 1

HCID 706056287-Chloro-5-phenyl-1,2,3,4-tetrahydro-2-nitromethylene-5H-1, 5-benzodiazepin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Potassium t-butoxide, 10.24 g (.092 moles) was added to a mixture of 250 ml of dimethylformamide and 50 ml of nitromethane. After stirring at room temperature for 15 min under nitrogen, 25 g (0.076 m) of 7-chloro-3,5-dihydro-2-(N-nitrosomethylamino)-5-phenyl-4H-1,5-benzodiazepin-4-one was added and stirring was continued for an additional 19 hours. The mixture was acidified with acetic acid and diluted with water. The precipitate was filtered off, washed with water and recrystallized from methylene chloride/ethanol to give pale yellow crystals with mp 259°-261°.

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for an additional 19 hours
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. customrecrystallized from methylene chloride/ethanol
  6. customto give pale yellow crystals with mp 259°-261°

Quellen und Nachweise

ORD-Eintrag
ord-1d3c4d45d37e405cbd644ac423749511
Quelldatensatz
uspto-grants-1978_03
Patentnummer
US04080323

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