Dimethyl Sulfate → 6-Methyl-2-(methylsulfanyl)cyclohepta[d]imidazole

HRID 359927Notes

Reaction equation

HRID 359927 reaction equation
[OH-].[K+].[SH:3][C:4]1[N:5]=[C:6]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=[C:7]2[N:8]=1.[CH3:15]OS(=O)(=O)OC>CO>[CH3:14][C:11]1[CH:12]=[CH:13][C:6]2[C:7](=[CH:9][CH:10]=1)[N:8]=[C:4]([S:3][CH3:15])[N:5]=2

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 178423442HCID 178423442, compound

Product 1

HCID 200643756-Methyl-2-(methylsulfanyl)cyclohepta[d]imidazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

38 g of potassium hydroxide was dissolved in 800 ml of methanol, and 108.5 g of 2-mercapto-6-methylcycloheptimidazole was added thereto and everything was stirred under heating at an internal temperature of about 45° C. Next, 131.2 g of dimethylsulfuric acid was dropwise added and everything was further stirred under heating at an internal temperature of about 45° C. for 1 hour. After the solvent was evaporated off to some extent under reduced pressure, 1 liter of water was added and the resulting solution was extracted with chloroform (0.5 liter×2). The chloroform layer was dried with anhydrous sodium sulfate, and then the solvent was evaporated off under reduced pressure until the chloroform solution became 200 ml. To this was added one liter of hexane, whereby crystals precipitated out. The thus formed crystals were separated by filtration and dried.

Workup

  1. stirringeverything was further stirred
  2. temperatureunder heating at an internal temperature of about 45° C. for 1 hour
  3. customAfter the solvent was evaporated off to some extent under reduced pressure, 1 liter of water
  4. additionwas added
  5. extractionthe resulting solution was extracted with chloroform (0.5 liter×2)
  6. dry with materialThe chloroform layer was dried with anhydrous sodium sulfate
  7. customthe solvent was evaporated off under reduced pressure until the chloroform solution
  8. additionTo this was added one liter of hexane, whereby crystals
  9. customprecipitated out
  10. customThe thus formed crystals were separated by filtration
  11. customdried

Sources & evidence

ORD record
ord-befbd74704784526b4f7d3d1cec1d524
Source dataset
uspto-grants-1991_03
Patent number
US05003077

Reaction notes

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