Potassium Iodide → HCID 21321305, compound

HRID 261971

Reaction equation

HRID 261971 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)([C:10]2[NH:11][CH:12]=[CH:13][N:14]=2)[OH:9])=[CH:4][CH:3]=1.[C:22]1(C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C=1)[N+]([O-])=O.[I-].[K+].[OH-].[Na+].CI>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)([C:10]2[N:14]([CH3:22])[CH:13]=[CH:12][N:11]=2)[OH:9])=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 6328Methyl iodideHCID 6954Picric AcidHCID 14798Sodium HydroxideHCID 12433870Bis-(4-chloro-phenyl)-(1H-imidazol-2-yl)-methanol

Product 1

HCID 21321305HCID 21321305, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a suspension of 9.6 g (0.030 mol) of α,α-bis(p-chlorophenyl)imidazole-2-methanol (prepared according to Example III) in 100 ml. of acetonitrile, 500 mg of picric acid, 300 mg of potassium iodide and 1.45 g (0.036 mol) of sodium hydroxide were added at 60° C. The reaction mixture was stirred for one hour and then 4.7 g (0.033 mol) of methyl iodide in 25 ml. of acetonitrile were added dropwise at 55° C. The mixture was refluxed for four hours, the solvent was distilled off and the residue was extracted with a mixture of water and diethyl ether. The solid matter was filtered off and the ethereal phase was dried over sodium sulphate and concentrated. Diethyl ether was added to the residue and the solid matter was filtered off. The two portions of solid material were combined and twice crystallised from isopropyl alcohol and twice from toluene and rewashed with petroleum ether (boiling range 60°-80° C.). α,α-Bis(p-chlorophenyl)-1-methylimidazole-2-methanol was obtained. Melting point 190°-191° C.

Workup

  1. temperatureThe mixture was refluxed for four hours
  2. distillationthe solvent was distilled off
  3. extractionthe residue was extracted with a mixture of water and diethyl ether
  4. filtrationThe solid matter was filtered off
  5. dry with materialthe ethereal phase was dried over sodium sulphate
  6. concentrationconcentrated
  7. additionDiethyl ether was added to the residue
  8. filtrationthe solid matter was filtered off
  9. customtwice crystallised from isopropyl alcohol and twice from toluene

Sources & evidence

ORD record
ord-fa1e8f200d2b431ba484ee83dd61595a
Source dataset
uspto-grants-1979_05
Patent number
US04152441

Linked notes

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