Dimethylformamide → HCID 70605160, compound

HRID 614711Notes

Reaction equation

HRID 614711 reaction equation
CC(C)([O-])C.[K+].CN(C)C=O.[N+:12]([CH3:15])([O-:14])=[O:13].N(CN[C:20]1[CH2:21][C:22](=[O:37])[N:23]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:24]2[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=2[N:26]=1)=O>O.C(O)(=O)C>[C:31]1([N:23]2[C:24]3[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=3[NH:26][C:20](=[CH:15][N+:12]([O-:14])=[O:13])[CH2:21][C:22]2=[O:37])[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6375NitromethaneHCID 23665647Potassium tert-butoxideHCID 178526372HCID 178526372, compound

Product 1

HCID 70605160HCID 70605160, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Potassium t-butoxide, 3.15 g (0.0281 moles) was added to a mixture of 70 ml of dimethylformamide and 14 ml of nitromethane. After stirring for 30 min at room temperature under nitrogen, 6.9 g (0.0234 moles) of 3,5-dihydro-2-(N-nitrosomethylamino)-5-phenyl-4H-1,5-benzodiazepin-4-one, was added and stirring was continued for 48 hours. The mixture was acidified with acetic acid and diluted with water. The precipitate was collected, washed with water and recrystallized from methylene chloride/ethanol to yield end product with mp 231°-234°. Recrystallization for analysis from the some solvents raised the melting point to 233°-235°.

Workup

  1. stirringstirring
  2. waitwas continued for 48 hours
  3. customThe precipitate was collected
  4. washwashed with water
  5. customrecrystallized from methylene chloride/ethanol
  6. customto yield end product with mp 231°-234°
  7. customRecrystallization for analysis from the some solvents
  8. temperatureraised the melting point to 233°-235°

Sources & evidence

ORD record
ord-e5d67f3b000c4261b61b4587902ee82b
Source dataset
uspto-grants-1979_03
Patent number
US04146537

Reaction notes

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