Imidazole → HCID 54257884, compound

HRID 1284075Notes

Reaction equation

HRID 1284075 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)Cl.C1(C)C=CC([Mg]Br)=CC=1.COC(C(=O)C1C=CC=CC=1)=O.P(Cl)(Cl)(Cl)(Cl)Cl.[NH:47]1[CH:51]=[CH:50][N:49]=[CH:48]1>C(#N)C>[CH3:1][O:2][C:3](=[O:19])[C:4]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)[C:48]1[NH:47][CH:51]=[CH:50][N:49]=1

Participants

7

Reactant 5

HCID 795ImidazoleHCID 24819Phosphorus pentachlorideHCID 84835Methyl phenylglyoxalateHCID 54543960HCID 54543960, compoundHCID 178418370HCID 178418370, compound

Product 1

HCID 54257884HCID 54257884, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

13.7 g phenyl-p-tolyl-chloroacetic acid methyl ester (prepared from p-tolyl-magnesium bromide and benzoyl-formic acid methyl ester and treatment with PCl5 ; (b.p. 150°C./0.3 mm Hg) are heated with 10 g imidazole in 100 ml acetonitrile at boiling temperature for 16 hours. The acetonitrile is distilled off in a vacuum. The residue is treated with 50 ml of water and then extracted with methylene chloride. The methylene chloride solution is distilled off in a vacuum and the residue recrystallized from a little ethyl acetate. The phenyl-p-tolyl-imidazolyl-acetic acid methyl ester i.e. phenyl-4-methylphenyl-imidazolyl-acetic acid methyl ester of m.p. 146°C. is thus obtained.

Workup

  1. customfor 16 hours
  2. distillationThe acetonitrile is distilled off in a vacuum
  3. additionThe residue is treated with 50 ml of water
  4. extractionextracted with methylene chloride
  5. distillationThe methylene chloride solution is distilled off in a vacuum
  6. customthe residue recrystallized from a little ethyl acetate

Sources & evidence

ORD record
ord-b3ff9e8f4dd448139a27b0d048847016
Source dataset
uspto-grants-1976_08
Patent number
US03978069

Reaction notes

Loading…