Acetyl chloride → 4-Acetylamino-1-benzyl-5-imidazolecarboxamide

HRID 382376Notes

Reaction equation

HRID 382376 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][N:5]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:6]=1[C:7]([NH2:9])=[O:8].C(N(CC)CC)C.[C:24](Cl)(=[O:26])[CH3:25]>CN(C)C=O>[C:24]([NH:1][C:2]1[N:3]=[CH:4][N:5]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:6]=1[C:7]([NH2:9])=[O:8])(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 140006201-benzyl-4-amino-1H-imidazole-5-carboxamide

Product 1

HCID 183603414-Acetylamino-1-benzyl-5-imidazolecarboxamideYield 33.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.2 g (10 mmol) of 4-amino-1-benzyl-5-imidazole carboxamide prepared in Reference Example 2 was dissolved in 200 ml of N,N-dimethylformamide. 2.1 ml (15 mmol) of triethylamine and 1.06 ml (15 mmol) of acetyl chloride were added to the mixture while cooling with ice, followed by stirring overnight. The reaction product was concentrated under vacuum to obtain a crude product, which was recrystallized from hot methanol to obtain 0.86 g of 4-acetylamino-1-benzyl-5-imidazolecarboxamide (yield 33%).

Workup

  1. temperaturewhile cooling with ice
  2. concentrationThe reaction product was concentrated under vacuum
  3. customto obtain a crude product, which
  4. customwas recrystallized from hot methanol

Sources & evidence

ORD record
ord-f5545f1bf7254fbdbb72ca56743e0fec
Source dataset
uspto-grants-2001_10
Patent number
US06310070B1

Reaction notes

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