Trimethyl orthoacetate → Methyl N-(5-cyanoimidazol-4-yl)acetimidate

HRID 1595206Notes

Reaction equation

HRID 1595206 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[C:7]#[N:8].[C:9](OC)(OC)([O:11][CH3:12])[CH3:10]>CN(C=O)C>[C:7]([C:6]1[NH:5][CH:4]=[N:3][C:2]=1[N:1]=[C:9]([O:11][CH3:12])[CH3:10])#[N:8]

Participants

4

Reactant 2

HCID 15050Trimethyl orthoacetateHCID 787775-amino-1H-imidazole-4-carbonitrile

Product 1

HCID 67550327Methyl N-(5-cyanoimidazol-4-yl)acetimidate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

5 g of 4-amino-5-cyanoimidazole was suspended in 10 mL of DMF and 10 mL of trimethyl orthoacetate was added, followed by stirring at 90° C. for 30 minutes. The reaction solution was concentrated under reduced pressure and the residue was dilute with ethyl acetate, and then 4.2 g of desired compound deposited as a crystal was collected by filtration. The solution was concentrated and the residue was purified by silica gel column chromatograpy (eluent: ethyl acetate) and then recrystallized from ethyl acetate-n-hexane to obtain 2.9 g of a desired compound as a crystal.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionthe residue was dilute with ethyl acetate
  3. filtrationwas collected by filtration
  4. concentrationThe solution was concentrated
  5. customthe residue was purified by silica gel column chromatograpy (eluent: ethyl acetate)
  6. customrecrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-02d1fcf416d447a689f103c7f65d514e
Source dataset
uspto-grants-2001_09
Patent number
US06288070B1

Reaction notes

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