Acetic Acid → HCID 178470215, compound

HRID 1595387Notes

Reaction equation

HRID 1595387 reaction equation
O[N:2]=[C:3]([C:9]([C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1)=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:18]([O:25][C:26]1[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([O-])(=O)C.[NH4+:38].C(O)(=O)C>O>[CH2:18]([O:25][C:26]1[CH:33]=[CH:32][C:29]([C:30]2[NH:38][C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:2]=2)=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 517165Ammonium AcetateHCID 178472891HCID 178472891, compound

Product 1

HCID 178470215HCID 178470215, compoundYield 46.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 2-hydroxyimino-3-(4-methylphenyl)-3-oxopropionate (44.9g), 4-benzyloxybenzaldehyde (61.0 g) and ammonium acetate (147 g) were added to acetic acid (400 ml) and themixturewas refluxed under heating for 17 hr. Water (1.5 L) was added and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried. The solvent was evaporated under reduced pressure and the obtained residue was recrystallized from ethyl acetate and ether to give ethyl 2-(4-benzyloxyphenyl)-5-(4-methylphenyl)-imidazole-4-carboxylate (36.9 g), melting point 168-170° C.

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for 17 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water, saturated aqueous sodium hydrogencarbonate solution and saturated brine
  5. customdried
  6. customThe solvent was evaporated under reduced pressure
  7. customthe obtained residue was recrystallized from ethyl acetate and ether

Sources & evidence

ORD record
ord-b5c4cadcba7646d0a86d69b1a63ee76e
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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