Benzaldehyde → 4-Benzylideneamino-5-imidazolecarboxamide

HRID 382361Notes

Reaction equation

HRID 382361 reaction equation
Cl.[NH2:2][C:3]1[N:4]=[CH:5][NH:6][C:7]=1[C:8]([NH2:10])=[O:9].C(N(CC)CC)C.[CH:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>C(O)C>[CH:18](=[N:2][C:3]1[N:4]=[CH:5][NH:6][C:7]=1[C:8]([NH2:10])=[O:9])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 962WaterHCID 8471TriethylamineHCID 661465-Aminoimidazole-4-carboxamide hydrochloride

Product 1

HCID 539704464-Benzylideneamino-5-imidazolecarboxamideYield 97.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

16.3 g (100 mmol) of 4-amino-5-imidazolecarboxamide hydrochloride was suspended in 200 ml ethanol, and 27.8 ml (200 mmol) of triethylamine was added to the suspension and dissolved. To the solution, 10.2 ml (100 mmol) of benzaldehyde was added and the mixture was heated for 8 hours while refluxing. After the addition of 400 ml of distilled water, the reaction mixture was stirred for one hour at 0° C. A solid precipitate produced was collected by filtration, washed with distilled water, then with ethanol, and dried under reduced pressure to obtain 20.8 g of the title compound (yield 97%).

Workup

  1. dissolutiondissolved
  2. temperaturethe mixture was heated for 8 hours
  3. temperaturewhile refluxing
  4. customA solid precipitate produced
  5. filtrationwas collected by filtration
  6. washwashed with distilled water
  7. dry with materialwith ethanol, and dried under reduced pressure

Sources & evidence

ORD record
ord-de6431ae773b4bcd9b792e1bd6fcfc05
Source dataset
uspto-grants-2001_10
Patent number
US06310070B1

Reaction notes

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