Propylamine → 5-Amino-1-propyl-1H-imidazole-4-carboxamide

HRID 3644

Reaction equation

HRID 3644 reaction equation
[NH2:1][CH:2]([C:6]#[N:7])[C:3]([NH2:5])=[O:4].[CH3:8]OC(OC)OC.[CH2:15]([NH2:18])[CH2:16][CH3:17]>C(#N)C>[NH2:7][C:6]1[N:18]([CH2:15][CH2:16][CH3:17])[CH:8]=[N:1][C:2]=1[C:3]([NH2:5])=[O:4]

Participants

5

Reactant 3

HCID 7852PropylamineHCID 9005Trimethyl orthoformateHCID 983412-Amino-2-cyanoacetamide

Product 1

HCID 123391055-Amino-1-propyl-1H-imidazole-4-carboxamideYield 61.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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%.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 0.75 hour
  3. temperatureto cool
  4. customThe solid which precipitated
  5. filtrationwas collected by filtration
  6. customcrystallised from methanol

Sources & evidence

ORD record
ord-12e40ee7e23541c4b9a7cdf8dcd80cd1
Source dataset
uspto-grants-1998_03
Patent number
US05734053

Linked notes

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