Methyl iodide → HCID 20275406, compound

HRID 1758253Notes

Reaction equation

HRID 1758253 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[CH:11][NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.[H-].[Na+].[CH3:24]I>CN(C)C=O>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[N:12]=[CH:11][N:10]([CH3:24])[C:9]=2[C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14100143HCID 14100143, compound

Product 1

HCID 20275406HCID 20275406, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 10.0 g. 4,5-bis(4-methoxyphenyl)imidazole in 100 ml of dimethylformamide was treated with 2.4 g of a 50% sodium hydride dispersion and then 8.0 g of methyl iodide was added dropwise. Stirring at room temperature was continued overnight and the reaction mixture was poured onto ice water. The product was collected by filtration and recrystallization from hot 1-chlorobutane gave 7.0 g of 4,5-bis(4-methoxyphenyl)-1-methyl-1H-imidazole, m.p. 121.5°-122°.

Workup

  1. additionthe reaction mixture was poured onto ice water
  2. filtrationThe product was collected by filtration and recrystallization from hot 1-chlorobutane

Sources & evidence

ORD record
ord-80bfd4d960ad49c2ab64abc3eb106a2a
Source dataset
uspto-grants-1983_02
Patent number
US04372964

Reaction notes

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