Iodoethane → 5-Amino-1-ethyl-1H-imidazole-4-carbonitrile

HRID 2186456Notes

Reaction equation

HRID 2186456 reaction equation
[NH2:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[C:7]#[N:8].C(=O)([O-])[O-].[K+].[K+].I[CH2:16][CH3:17]>O1CCCC1.CN(C)C=O>[NH2:1][C:2]1[N:6]([CH2:16][CH3:17])[CH:5]=[N:4][C:3]=1[C:7]#[N:8]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178510601HCID 178510601, compound

Product 1

HCID 184236595-Amino-1-ethyl-1H-imidazole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To a solution/suspension of 5-amino-1H-imidazole-4-carbonitrile (2.16 g) in tetrahydrofuran/N,N-dimethylformamide under an atmosphere of nitrogen was added potassium carbonate (3.3 g) and iodoethane (1.9 mL). The reaction mixture was stirred at room temperature for 60 hours, filtered and the solvent removed in vacuo. Purification by column chromatography on silica eluting with 2-5% methanol in dichloromethane afforded the title compound as an off-white solid (0.60 g).

Workup

  1. filtrationfiltered
  2. customthe solvent removed in vacuo
  3. customPurification by column chromatography on silica eluting with 2-5% methanol in dichloromethane

Sources & evidence

ORD record
ord-905efa5990d44a5093a3b3f0154d36d5
Source dataset
uspto-grants-2002_06
Patent number
US06403791B1

Reaction notes

Loading…