Acetic Acid → HCID 178470180, compound

HRID 277713Notes

Reaction equation

HRID 277713 reaction equation
C([NH:3][C:4](=O)[C:5]([O-:7])=S)C.Cl.[NH2:10][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O.[C:20]([O-])(=O)[CH3:21].[Na+].C(O)(=[O:27])C>>[C:14]1([C:12]2[N:3]=[C:4]([C:5]([O:7][CH2:20][CH3:21])=[O:27])[NH:10][CH:11]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 2723597Ethanone, 2-amino-1-phenyl-, hydrochloride (1:1)HCID 178465254HCID 178465254, compound

Product 1

HCID 178470180HCID 178470180, compound

Procedure

A mixture of 3 g of ethylthiooxamate, 4.25 g of 2-aminoacetophenone hydrochloride and 3.69 g of sodium acetate was dissolved in 20 mL of acetic acid and heated under reflux for 3 hr. The reaction mixture was allowed to cool to room temperature and the acetic acid removed by evaporation under reduced pressure. The residue was basified with aqueous sodium carbonate and extracted with 2×100 mL of ethyl acetate. The combined extracts were washed with 2×100 mL of brine, dried over anhydrous sodium sulfate and the solvent removed under reduced pressure to yield 2.8 g of ethyl 4-phenylimidazole-2-carboxylate as a solid which was used in the next step without further purification or characterization.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hr
  3. customthe acetic acid removed by evaporation under reduced pressure
  4. extractionextracted with 2×100 mL of ethyl acetate
  5. washThe combined extracts were washed with 2×100 mL of brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-e0a7b701a3b44b63b0698ad289e1d9e0
Source dataset
uspto-grants-2002_03
Patent number
US06358955B1

Reaction notes

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