Dimethyl Sulfate → HCID 12833691, compound

HRID 484662Notes

Reaction equation

HRID 484662 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-afd04c6dd70b4fc496b90826082f0450
Source dataset
uspto-grants-1985_08
Patent number
US04533550

Reaction notes

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