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

HRID 1194296Notes

Reaction equation

HRID 1194296 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.S(OC)(O[CH3:19])(=O)=O>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][CH3:19])[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

First, 38 g of potassium hydroxide was dissolved in 800 ml of methanol, 108.5 g of 2-mercapto-6-methycycloheptimidazole was added, 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 in some extent under reduced pressure, 1 l of water was added and extracted with chloroform (0.5 l×2). The chloroform layer was dried over anhydrous sodium sulfate and evaporated to 200 ml under reduced pressure to distil away the solvent. With the addition of 1 l of hexane, crystals were deposited, and they were collected by filtration 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 in some extent under reduced pressure, 1 l of water
  4. additionwas added
  5. extractionextracted with chloroform (0.5 l×2)
  6. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  7. customevaporated to 200 ml under reduced pressure
  8. customto distil away the solvent
  9. additionWith the addition of 1 l of hexane, crystals
  10. filtrationthey were collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-a7057ce3ec4c451d9e1077fe477fb83d
Source dataset
uspto-grants-1989_03
Patent number
US04814265

Reaction notes

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