Dimethyl Sulfate → HCID 12877073, compound

HRID 2286554Notes

Reaction equation

HRID 2286554 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)[C:4](=[O:7])[NH:5][N:6]=1.[H-].[Na+].S(OC)(O[CH3:23])(=O)=O>CS(C)=O>[CH3:23][N:5]1[C:4](=[O:7])[N:3]([C:8]2[CH:9]=[CH:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=2)[C:2]([CH3:1])=[N:6]1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 12877072HCID 12877072, compound

Product 1

HCID 12877073HCID 12877073, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of 13.5 parts of 2,4-dihydro-5-methyl-4-(4-nitrophenyl)-3H-1,2,4-triazol-3-one in 100 parts of dimethyl sulfoxide are added 2 parts of sodium hydride dispersion 78% and the whole is stirred till foaming has ceased. Then there are added dropwise 8.1 parts of dimethyl sulfate. Upon completion, stirring is continued for 3 hours at room temperature. The reaction mixture is poured onto water and the product is extracted three times with trichloromethane. The combined extracts are washed with water, dried, filtered and evaporated. The residue is crystallized from a mixture of 2-propanol and 2,2'-oxybispropane. The product is filtered off and recrystallized from 4-methyl-2-pentanone, yielding 6.3 parts of 2,4-dihydro-2,5-dimethyl-4-(4-nitrophenyl)-3H-1,2,4-triazol-3-one; mp. 153.2° C.

Workup

  1. stirringUpon completion, stirring
  2. additionThe reaction mixture is poured onto water
  3. extractionthe product is extracted three times with trichloromethane
  4. washThe combined extracts are washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is crystallized from a mixture of 2-propanol and 2,2'-oxybispropane
  9. filtrationThe product is filtered off
  10. customrecrystallized from 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-5a322ea66e0f4f94928c8031e58cdb27
Source dataset
uspto-grants-1981_05
Patent number
US04267179

Reaction notes

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