Ammonia → HCID 45120975, compound

HRID 2356750Notes

Reaction equation

HRID 2356750 reaction equation
[CH:1]([NH:3][CH:4]([CH2:13][CH3:14])[C:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=O)=O.C([O-])(=O)C.[NH4+:19].N>C(O)(=O)C>[CH2:13]([C:4]1[NH:3][CH:1]=[N:19][C:5]=1[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)[CH3:14]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 517165Ammonium AcetateHCID 86593203HCID 86593203, compound

Product 1

HCID 45120975HCID 45120975, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-formylamino-1-(3-pyridyl)-1-butanone (640 mg) and ammonium acetate (5.13 g) in acetic acid (5 ml) was stirred at 100° C. for 1.5 hours. After cooling, 28% aqueous ammonia was added to the reaction mixture and the mixture was extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The resulting residue was triturated with ethyl acetate-diethyl ether to obtain 5-ethyl-4-(3-pyridyl)imidazole (520 mg) as colorless powder.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe resulting residue was triturated with ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-951969bed7c842c3b29901f42e74bd09
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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