Methyl iodide → HCID 13048892, compound

HRID 542378Notes

Reaction equation

HRID 542378 reaction equation
[CH3:1][C:2]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:3]=1[CH2:4][C:5]1[N:6]=[CH:7][NH:8][CH:9]=1.[CH3:15]I.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:3]=1[CH2:4][C:5]1[N:6]=[CH:7][N:8]([CH3:15])[CH:9]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 178424776HCID 178424776, compound

Product 1

HCID 13048892HCID 13048892, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

3.0 g of 4-(2',6'-dimethylbenzyl)-imidazole, 40 ml of toluene, 3.0 g of methyliodide, 0.14 g of tetrabutylammoniumhydrogensulfate and 40 ml of 48% sodium hydroxide are mixed. The mixture is stirred vigorously for 2 hours at 70° C., after which the mixture is cooled and filtered. The toluene layer is separated from the mother liquid, after which it is washed with water and evaporated to dryness. The residue is a mixture of 4-(2',6'-dimethylbenzyl)-3-methylimidazole and 4-(2',6'-dimethylbenzyl)-1-methylimidazole. These two components are separated column chromatographically, eluting the column with a mixture of chloroform and methanol.

Workup

  1. temperatureafter which the mixture is cooled
  2. filtrationfiltered
  3. customThe toluene layer is separated from the mother liquid
  4. washafter which it is washed with water
  5. customevaporated to dryness
  6. additiona mixture of 4-(2',6'-dimethylbenzyl)-3-methylimidazole and 4-(2',6'-dimethylbenzyl)-1-methylimidazole
  7. customThese two components are separated column chromatographically
  8. washeluting the column
  9. additionwith a mixture of chloroform and methanol

Sources & evidence

ORD record
ord-320dd4578f2745b58dca38de50d43564
Source dataset
uspto-grants-1987_04
Patent number
USRE032400

Reaction notes

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