Sodium Hydroxide → 1-benzyl-4-amino-1H-imidazole-5-carboxamide

HRID 382363Notes

Reaction equation

HRID 382363 reaction equation
Cl.[NH2:2][C:3]1[N:4]=[CH:5][N:6]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]=1[C:8]([NH2:10])=[O:9].[OH-].[Na+]>CO.O>[NH2:2][C:3]1[N:4]=[CH:5][N:6]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]=1[C:8]([NH2:10])=[O:9]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 183603364-Amino-1-benzyl-5-imidazole carboxamide hydrochloride

Product 1

HCID 140006201-benzyl-4-amino-1H-imidazole-5-carboxamideYield 94.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

9.12 g (30 mol) of 4-benzylideneamino-1-benzyl-5-imidazolecarboxamide obtained was dissolved in 135 ml of tetrahydrofuran. After the addition of 15 ml of concentrated hydrochloric acid, the mixture was stirred at room temperature for two hours. The precipitate obtained was separated by filtration and washed with tetrahydrofuran to obtain 7.26 g of 4-amino-1-benzyl-5-imidazolecarboxamide hydrochloride. 7.26 g of the 4-amino-1-benzyl-5-imidazole carboxamide hydrochloride obtained was dissolved in a mixed solvent of 100 ml of methyl alcohol and 80 ml of distilled water. After the addition of 7.5 ml of 4 N aqueous solution of sodium hydroxide, the mixture was stirred at room temperature for one hour. Methanol was evaporated and the resulting precipitate separated by filtration was washed with distilled water and ethanol to obtain 5.85 g of the title compound (yield 90%) (2 steps).

Workup

  1. customMethanol was evaporated
  2. customthe resulting precipitate separated by filtration
  3. washwas washed with distilled water and ethanol

Sources & evidence

ORD record
ord-83f0dc67c0154cc49a566396b89ae717
Source dataset
uspto-grants-2001_10
Patent number
US06310070B1

Reaction notes

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