Reaction #3740

Reaction equation

2-amino-2-cyanoacetamide

trimethylorthoformate

n-Propylamine

→

title compound

Yield 61.1%

5-Amino-1-n-propylimidazole-4-carboxamide

Yield 61.1%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureunder reflux for 0.75 hour
3. 3
   Temperatureto cool
4. 4
   OtherThe solid which precipitated
5. 5
   Filtrationwas collected by filtration
6. 6
   Othercrystallised from methanol

Procedure

A mixture of 2-amino-2-cyanoacetamide (2.8 g, 0.0282 mol), trimethylorthoformate (3.4 g, 0.0321 mol) and acetonitrile (55 ml) was heated under reflux for 0.75 hour, then allowed to cool. n-Propylamine (1.8 g, 0.0305 mol) was then added dropwise, and the resulting mixture stirred at ambient temperature for 36 hours. The solid which precipitated was collected by filtration and crystallised from methanol to give the title compound as a colourless solid (2.9 g, 61%), m.p. 241°-243° C. Found: C,49.67; H,7.15; N,33.64. C7 H12N4O requires C,49.98; H,7.19; N,33.31%.

Source