Imidazole → HCID 54064871, compound

HRID 1284077Notes

Reaction equation

HRID 1284077 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)Cl)[CH3:2].[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1>C(#N)C>[C:1]1([O:3][C:4](=[O:20])[CH:5]([C:7]2[CH:8]=[CH:9][C:10]([Cl:13])=[CH:11][CH:12]=2)[C:14]2[NH:23][CH:24]=[CH:25][N:21]=2)[CH:2]=[CH:8][CH:7]=[CH:5][CH:4]=1.[CH2:1]([O:3][C:4](=[O:20])[C:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)[C:22]1[NH:21][CH:25]=[CH:24][N:23]=1)[CH3:2]

Participants

5

Reactant 2

HCID 795ImidazoleHCID 54184055HCID 54184055, compound

Product 2

HCID 54064871HCID 54064871, compoundHCID 131710441HCID 131710441, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

15.45 g (0.05 mole) phenyl-p-chlorophenyl-chloroacetic acid ethyl ester (prepared from p-chlorophenyl-magnesium bromide and benzoyl-formic acid ethyl ester and subsequent treatment with thionyl chloride: b.p. 160°C./0.2 mm Hg) are boiled with 10 g imidazole in 100 ml acetonitrile for 16 hours. After distilling off the solvent, 50 ml of water are added, and the mixture is extracted with methylene chloride. After drying, the solvent is distilled off in a vacuum and the phenyl-p-chlorophenyl-imidazolyl-acetate acid ethyl ester i.e. phenyl-4-chlorophenyl-imidazolyl-acetic acid ethyl ester is obtained in the form of an oil which solidifies after a fairly long time.

Workup

  1. distillationAfter distilling off the solvent, 50 ml of water
  2. additionare added
  3. extractionthe mixture is extracted with methylene chloride
  4. customAfter drying
  5. distillationthe solvent is distilled off in a vacuum

Sources & evidence

ORD record
ord-234f34edc37c4c428730a78dbc105fbd
Source dataset
uspto-grants-1976_08
Patent number
US03978069

Reaction notes

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