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

HRID 1679288Notes

Reaction equation

HRID 1679288 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

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°.

Workup

  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°

Sources & evidence

ORD record
ord-1d3c4d45d37e405cbd644ac423749511
Source dataset
uspto-grants-1978_03
Patent number
US04080323

Reaction notes

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