Dimethyl Sulfate → 2-Methylthiocycloheptimidazole

HRID 359921Notes

Reaction equation

HRID 359921 reaction equation
[OH-].[K+].[SH:3][C:4]1[N:5]=[C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=[C:7]2[N:8]=1.[CH3:14]OS(=O)(=O)OC>CO>[CH3:14][S:3][C:4]1[N:8]=[C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[N:5]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 178527782HCID 178527782, compound

Product 1

HCID 151230382-MethylthiocycloheptimidazoleYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

38 g of potassium hydroxide was dissolved in 800 ml of methanol and then 100 g of 2-mercaptocycloheptimidazole was added thereto and stirred under heating at an internal temperature of about 45° C. Next, 131.2 g of dimethylsulfuric acid was dropwise added and further stirred under heating at an internal temperature of about 45° C. for 1 hour. After the solvent was evaporated off to some degree under reduced pressure, one liter of water was added, and the resulting solution was extracted with chloroform (0.5 liter×2). Then, the chloroform layer was dried with anhydrous sodium sulfate, and the solvent was evaporated off under reduced pressure until the chloroform solution became 200 ml. Next, one liter of hexane was added to the thus concentrated solution whereby a precipitate crystallized out. This was separated by filtration and dried. 89 g of colorless crystals was obtained.

Workup

  1. stirringfurther stirred
  2. temperatureunder heating at an internal temperature of about 45° C. for 1 hour
  3. customAfter the solvent was evaporated off to some degree under reduced pressure, one liter of water
  4. additionwas added
  5. extractionthe resulting solution was extracted with chloroform (0.5 liter×2)
  6. dry with materialThen, the chloroform layer was dried with anhydrous sodium sulfate
  7. customthe solvent was evaporated off under reduced pressure until the chloroform solution
  8. additionNext, one liter of hexane was added to the thus concentrated solution whereby a precipitate
  9. customcrystallized out
  10. customThis was separated by filtration
  11. customdried

Sources & evidence

ORD record
ord-00e4f07391144a5787847956767a6f4d
Source dataset
uspto-grants-1991_03
Patent number
US05003077

Reaction notes

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