Dimethylformamide → HCID 70605160, compound

HRID 2163818Notes

Reaction equation

HRID 2163818 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 same 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 same solvents
  8. temperatureraised the melting point to 233°-235°

Sources & evidence

ORD record
ord-3a591b7a476e42308a0c5f0b0e31ed14
Source dataset
uspto-grants-1979_01
Patent number
US04137229

Reaction notes

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