Acetic Acid → alpha,alpha-Bis(2,4-dichlorophenyl)imidazole-2-methanol

HRID 261960Notes

Reaction equation

HRID 261960 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=1[Cl:26])([C:11]1[N:12](COC)[CH:13]=[CH:14][N:15]=1)[OH:10].C(O)(=O)C.Cl>O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=1[Cl:26])([C:11]1[NH:15][CH:14]=[CH:13][N:12]=1)[OH:10]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 12433909alpha,alpha-Bis(2,4-dichlorophenyl)-1-(methoxymethyl)imidazole-2-methanol

Product 1

HCID 12433874alpha,alpha-Bis(2,4-dichlorophenyl)imidazole-2-methanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 10 g (0.023 mol) of α,α-bis(2,4-dichlorophenyl)-1-(methoxymethyl)imidazole-2-methanol in 150 ml. of glacial acetic acid, 15 ml. of concentrated hydrochloric acid and 15 ml. of water was refluxed for two hours and then concentrated. The residue was dissolved in a small amount of a mixture of ethanol and 2N hydrochloric acid and the solution was extracted with diethyl ether. The extract was dried over sodium sulphate and the ether was distilled off. Diethyl ether and petroleum ether (boiling range 60°-80° C.) were added, the solid substance was filtered off and twice crystallised from isopropyl alcohol with a little ethanol. α,α-Bis(2,4-dichlorophenyl)imidazole-2-methanol was obtained. Melting point 193° C.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in a small amount of a mixture of ethanol and 2N hydrochloric acid
  3. extractionthe solution was extracted with diethyl ether
  4. dry with materialThe extract was dried over sodium sulphate
  5. distillationthe ether was distilled off
  6. additionDiethyl ether and petroleum ether (boiling range 60°-80° C.) were added
  7. filtrationthe solid substance was filtered off
  8. customtwice crystallised from isopropyl alcohol with a little ethanol

Sources & evidence

ORD record
ord-10440b84c3d940bfab89d4a4ea5e8fa5
Source dataset
uspto-grants-1979_05
Patent number
US04152441

Reaction notes

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