Water → HCID 178470174, compound

HRID 1595315Notes

Reaction equation

HRID 1595315 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].[C:18]1([CH2:28][NH2:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1.O>C1(C)C(C)=CC=CC=1>[CH3:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[NH:29][C:28]([C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=[CH:20][CH:19]=3)=[N:2][C:3]=2[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 83551-NaphthalenemethanamineHCID 178472891HCID 178472891, compound

Product 1

HCID 178470174HCID 178470174, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Ethyl 2-hydroxyimino-3-(4-methylphenyl)-3-oxopropionate (13.7 g) and 1-naphthalenemethylamine (11.0 g) were dissolved in xylene (137 ml), andrefluxed underheating for 9 hr whiledehydrating with Dean-stark trap. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried. The solvent was concentrated under reduced pressure and isopropyl alcohol was added to the obtained residue to allow crystallization. The crystals were collected by filtration to give ethyl 5-(4-methylphenyl)-2-(1-naphthyl)-imidazole-4-carboxylate (2.5 g), melting point 190-192° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationThe solvent was concentrated under reduced pressure and isopropyl alcohol
  5. additionwas added to the obtained residue
  6. customcrystallization
  7. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-cbbbe388db8b49608e8aa613f70d0897
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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