5-Aminoimidazole-4-carboxamide hydrochloride → HCID 14677479, compound

HRID 1199950Notes

Reaction equation

HRID 1199950 reaction equation
C[N:2]([CH3:16])[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=1)=O.Cl.NC1[N:20]=[CH:21][NH:22][C:23]=1[C:24]([NH2:26])=[O:25]>C(O)(=O)C>[N+:13]([C:9]1[CH:8]=[C:7]([C:5]2[N:20]3[CH:21]=[N:22][C:23]([C:24]([NH2:26])=[O:25])=[C:16]3[N:2]=[CH:3][CH:4]=2)[CH:12]=[CH:11][CH:10]=1)([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 661465-Aminoimidazole-4-carboxamide hydrochlorideHCID 608949HCID 608949, compound

Product 1

HCID 14677479HCID 14677479, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred mixture of 18.0 g of 3-dimethylamino-3'-nitroacrylophenone (prepared as described in Example 10) and 10.30 g of 4-amino-5-imidazolecarboxamide hydrochloride in 450 ml of glacial acetic acid was heated at reflux for 24 hours. Upon standing at room temperature a crystalline precipitate was formed. The precipitate was collected, washed with saturated sodium bicarbonate solution and then with water to give 13.1 g of product. The material was recrystallized from methanol-chloroform by the addition of hexane and by scratching to give 8.7 g of the product of the example as yellow crystals, mp 282°-284° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. customUpon standing at room temperature
  4. customwas formed
  5. customThe precipitate was collected
  6. washwashed with saturated sodium bicarbonate solution

Sources & evidence

ORD record
ord-494342790d1045b8b7be4b7c4513102f
Source dataset
uspto-grants-1990_02
Patent number
US04904658

Reaction notes

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