Dimethylformamide → HCID 12952790, compound

HRID 1263255Notes

Reaction equation

HRID 1263255 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([N:15]3[CH:19]=[N:18][NH:17][C:16]3=[O:20])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[H-].[Na+].[CH3:23]N(C)C=O.S(OC)(OC)(=O)=O>O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([N:15]3[CH:19]=[N:18][N:17]([CH3:23])[C:16]3=[O:20])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 20455087HCID 20455087, compound

Product 1

HCID 12952790HCID 12952790, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.5 parts of 2,4-dihydro-4-[4-(4-methoxyphenyl)-1-piperazinyl]-3H-1,2,4-triazol-3-one, 0.8 parts of sodium hydride dispersion 78% and 27 parts of N,N-dimethylformamide is stirred for one hour at room temperature. Then there are added 2.5 parts of dimethyl sulfate and stirring at room temperature is continued for another hour. Water is added to the reaction mixture and the product is extracted twice with dichloromethane. The extract is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions are collected and the eluent is evaporated, yielding 3.3 parts (71%) of 2,4-dihydro-4-[4-(4-methoxyphenyl)-1-piperazinyl]-2-methyl-3H-1,2,4-triazol-3-one; mp. 178.2° C.

Workup

  1. stirringstirring at room temperature
  2. waitis continued for another hour
  3. extractionthe product is extracted twice with dichloromethane
  4. customThe extract is dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  9. customThe pure fractions are collected
  10. customthe eluent is evaporated

Sources & evidence

ORD record
ord-33ac9c0d651845d182642d13dc41d9e9
Source dataset
uspto-grants-1984_06
Patent number
US04456605

Reaction notes

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