5-Aminoimidazole-4-carboxamide hydrochloride → Pur003

HRID 373638Notes

Reaction equation

HRID 373638 reaction equation
Cl.[NH2:2][C:3]1[N:4]=[CH:5][NH:6][C:7]=1[C:8]([NH2:10])=[O:9].Cl.[C:12](N)(=N)[CH3:13].C([O-])(=O)C.[Na+]>[OH-].[Na+]>[CH3:12][C:13]1[NH:10][C:8](=[O:9])[C:7]2[NH:6][CH:5]=[N:4][C:3]=2[N:2]=1

Participants

5

Reactant 3

HCID 661465-Aminoimidazole-4-carboxamide hydrochlorideHCID 67170Acetamidine monohydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 135449674Pur003

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
190 °C

Procedure

A solid mix of 4-amino-5-imidazolecarboxamide hydrochloride (30.75 mmol, 5 g) and acetamidine hydrochloride (2 eq, 61.5 mmol, 5.8 g) and sodium acetate (3 eq, 92.25 mmol, 7.6 g) were heated at 190° C. for 1 h. To the resultant off-white solid, at RT, NaOH (100 ml) was added and a white ppt was filtered away. The filtrate was acidified to pH 6.0 with AcOH (5 ml) and the resultant ppt filtered away. Both precipitates were dried separately in a vacuum oven at 80° C. for 24 h. The combined weight of pure product was (4.16 g, 90%). The first precipitate (2.11 g) analyzed as follows: mp.>300° C. DCI/MS (M+1)=151. (300 MHz) 1H-nmr (DMSO-d6)δ: 8.0 (s, 1H), 2.3 (s, 3H).

Workup

  1. filtrationa white ppt was filtered away
  2. filtrationthe resultant ppt filtered away
  3. customBoth precipitates were dried separately in a vacuum oven at 80° C. for 24 h

Sources & evidence

ORD record
ord-8c1e23865ea04e46b2e720cf3fc4d575
Source dataset
uspto-grants-1992_11
Patent number
US05164390

Reaction notes

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