Methyl iodide → HCID 13247650, compound

HRID 543330Notes

Reaction equation

HRID 543330 reaction equation
[Mg].[CH3:2]I.[N:4]1([C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:23])[C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[CH:11][N:10]=2)[CH:8]=[CH:7][N:6]=[CH:5]1.[Cl-].[NH4+]>CCOCC>[N:4]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)([OH:23])[CH3:2])=[CH:11][N:10]=2)[CH:8]=[CH:7][N:6]=[CH:5]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 13247703HCID 13247703, compound

Product 1

HCID 13247650HCID 13247650, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A Grignard reagent which is prepared by reacting 0.46 g of magnesium with 3 g of methyl iodide in 30 ml of ether is added to a suspension of 4.5 g of 2-(1-imidazolyl)-5-(4-chlorobenzoyl)pyridine in 50 ml of ether at -5° C. After the mixture is stirred at room temperature for an hour, the reaction mixture is poured into an aqueous ammonium chloride solution with caution. The precipitate is extracted with chloroform and the chloroform is distilled off. The residue is recrystallized from toluene to give 4.1 g of 1-[2-(1-imidazolyl)-5-pyridyl]-1-(4-chlorophenyl)ethanol in 90.3% yields as white crystals, melting at 140°-142° C.

Workup

  1. extractionThe precipitate is extracted with chloroform
  2. distillationthe chloroform is distilled off
  3. customThe residue is recrystallized from toluene

Sources & evidence

ORD record
ord-450152042aa342b8bf41de39a11dff08
Source dataset
uspto-grants-1987_04
Patent number
US04661603

Reaction notes

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