Acetic Acid → HCID 12433875, compound

HRID 261961Notes

Reaction equation

HRID 261961 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)([C:13]2[N:14](COC)[CH:15]=[CH:16][N:17]=2)[OH:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.Cl.C>C(OCC)C.C(O)(C)C.O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([C:21]2[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=2)([C:13]2[NH:17][CH:16]=[CH:15][N:14]=2)[OH:12])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 297MethaneHCID 313Hydrochloric AcidHCID 4450498HCID 4450498, compound

Product 1

HCID 12433875HCID 12433875, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of 13 g (0.034 mol) of α-(p-tert.-butylphenyl)-α-(p-chlorophenyl)-1-(methoxymethyl)imidazole-2-methanol, 150 ml. of glacial acetic acid, 15 ml. of concentrated hydrochloric acid and 15 ml. of water was refluxed for 31/2 hours. The reaction mixture was treated with active charcoal and concentrated. The residue was dissolved in diethyl ether and the solution was washed with water. To the ethereal phase an ethereal solution of oxalic acid was added. The precipitate thus formed was crystallised from ethanol with a small amount of methanol. The base was liberated by addition of sodium hydroxyde and extraction with diethyl ether. The ether was distilled off and the residue was crystallised from isopropyl alcohol. As the product obtained contained crystal isopropyl alcohol, it was dissolved in diethyl ether. The ethereal phase was washed with water and dried over sodium sulphate and the ether was distilled off. α-(p-tert.-Butylphenyl)-α-(p-chlorophenyl)imidazole-2-methanol was obtained. Melting point 95°-110° C. The melting point was not sharp but the NMR and IR spectra, the titrations and the elementary analysis were in conformity with the desired structure. Thin layer chromatography revealed only one component.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in diethyl ether
  3. washthe solution was washed with water
  4. additionTo the ethereal phase an ethereal solution of oxalic acid was added
  5. customThe precipitate thus formed
  6. customwas crystallised from ethanol with a small amount of methanol
  7. additionThe base was liberated by addition of sodium hydroxyde and extraction with diethyl ether
  8. distillationThe ether was distilled off
  9. customthe residue was crystallised from isopropyl alcohol
  10. customAs the product obtained
  11. washThe ethereal phase was washed with water
  12. dry with materialdried over sodium sulphate
  13. distillationthe ether was distilled off

Sources & evidence

ORD record
ord-dc48cd05ade9423dac8b36e209e8d080
Source dataset
uspto-grants-1979_05
Patent number
US04152441

Reaction notes

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