Dimethylformamide → 4-Benzylideneamino-1-benzyl-5-imidazole carboxamide

HRID 382362Notes

Reaction equation

HRID 382362 reaction equation
[CH:1](=[N:8][C:9]1[N:10]=[CH:11][NH:12][C:13]=1[C:14]([NH2:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[CH2:28](Cl)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O>[CH:1](=[N:8][C:9]1[N:10]=[CH:11][N:12]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:13]=1[C:14]([NH2:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 539704464-Benzylideneamino-5-imidazolecarboxamide

Product 1

HCID 545640564-Benzylideneamino-1-benzyl-5-imidazole carboxamideYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

12.8 g (60 mmol) of 4-benzylideneamino-5-imidazole carboxamide which is an intermediate material obtained in the Reference Example 1 was suspended in a mixed solvent of 240 ml dimethylformamide and 30 ml distilled water, and 16.6 g (120 mmol) of potassium carbonate was added to the suspension. 13.8 ml of benzyl chloride was added dropwise to the solution over 45 minutes at 80° C. After the addition, the mixture was stirred for one hour. The solvent was evaporated under vacuum, the residue was dissolved in chloroform, and the chloroform layer was washed with distilled water. Crude crystals obtained after evaporation of solvent was recrystallized from ethanol to obtain 14.4 g of 4-benzylideneamino-1-benzyl-5-imidazole carboxamide (yield 79%).

Workup

  1. customobtained in the Reference Example 1
  2. additionwas added to the suspension
  3. additionAfter the addition
  4. customThe solvent was evaporated under vacuum
  5. dissolutionthe residue was dissolved in chloroform
  6. washthe chloroform layer was washed with distilled water
  7. customCrude crystals obtained
  8. customafter evaporation of solvent
  9. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-7e8d16b7acf44e12a9c83a4bc8823eba
Source dataset
uspto-grants-2001_10
Patent number
US06310070B1

Reaction notes

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