Dimethyl Sulfate → 2-Methylthiocycloheptimidazole

HRID 1199338Notes

Reaction equation

HRID 1199338 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.S(OC)(O[CH3:18])(=O)=O>CO>[CH3:18][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-Methylthiocycloheptimidazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

First, 38 g of potassium hydroxide was dissolved in 800 ml of methanol, 100 g of 2-mercaptocycloheptimidazole was added thereto, and the mixture was stirred with heating to the inner temperature of about 45° C. Then, 131.2 g of dimethyl sulfate was added dropwise thereto and stirred with heating to the inner temperature of about 45° C. for one hour. After the solvent was distilled away to some extent under reduced pressure, 1 l of water was added and extracted with chloroform (0.5 l×2). After being dried over anhydrous sodium sulfate, the chloroform layer was evaporated under reduced pressure to 200 ml, and 1 l of hexane was added thereto to deposit crystals, which were the filtered and dried.

Workup

  1. stirringstirred
  2. temperaturewith heating to the inner temperature of about 45° C. for one hour
  3. distillationAfter the solvent was distilled away to some extent under reduced pressure, 1 l of water
  4. additionwas added
  5. extractionextracted with chloroform (0.5 l×2)
  6. dry with materialAfter being dried over anhydrous sodium sulfate
  7. customthe chloroform layer was evaporated under reduced pressure to 200 ml, and 1 l of hexane
  8. additionwas added
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-f2554bd6e29349688801b55dc1b406c1
Source dataset
uspto-grants-1990_02
Patent number
US04900648

Reaction notes

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