Dimethyl Sulfate → HCID 12833691, compound

HRID 1446845Notes

Reaction equation

HRID 1446845 reaction equation
[OH-].[K+].[CH2:3]([N:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[N:7]=[C:6]1[SH:17])[CH3:4].S(OC)(O[CH3:22])(=O)=O>CO>[CH2:3]([N:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[N:7]=[C:6]1[S:17][CH3:22])[CH3:4]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 178462493HCID 178462493, compound

Product 1

HCID 12833691HCID 12833691, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 3.25 parts of potassium hydroxide solution 86% in 80 parts of methanol are added 11 parts of 4-(1-ethyl-2-mercapto-1H-imidazol-4-yl)phenol and stirring is continued till all solid enters solution. Then there are added 6.9 parts of dimethyl sulfate and the whole is stirred overnight at room temperature. The precipitate is filtered off and the filtrate is evaporated. The solid residue is stirred with water. The product is filtered off and crystallized from 4-methyl-2-pentanone, yielding 7 parts (60%) of 4-[1-ethyl-2-(methylthio)-1H-imidazol-4-yl]phenol; mp. 218.2° C.

Workup

  1. stirringthe whole is stirred overnight at room temperature
  2. filtrationThe precipitate is filtered off
  3. customthe filtrate is evaporated
  4. stirringThe solid residue is stirred with water
  5. filtrationThe product is filtered off
  6. customcrystallized from 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-59ccf8d269a140779449bd038cb758d6
Source dataset
uspto-grants-1982_02
Patent number
US04313953

Reaction notes

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