1H-1,2,4-Triazole → HCID 13655350, compound

HRID 745280Notes

Reaction equation

HRID 745280 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[H-].[Na+].CS(O[CH2:13][CH:14]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=1[Cl:23])[CH3:15])(=O)=O>CN(C)C=O>[Cl:23][C:17]1[CH:18]=[C:19]([Cl:22])[CH:20]=[CH:21][C:16]=1[CH:14]([CH3:15])[CH2:13][N:1]1[CH:5]=[N:4][CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 13655349HCID 13655349, compound

Product 1

HCID 13655350HCID 13655350, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 14 parts of 1H-1,2,4-triazole and 225 parts of N,N-dimethylformamide are added 6.2 parts of a sodium hydride dispersion 78%. When foaming has ceased, there are added 19.5 parts of 2-(2,4-dichlorophenyl)propyl methanesulfonate and stirring is continued for 6 hours at reflux. The reaction mixture is cooled, poured onto water and the product is extracted twice with 2,2'-oxybispropane. The combined extracts are washed with water, dried, filtered and evaporated. The residue is crystallized from petroleumether. The product is filtered off and dried, yielding 10.2 parts (58%) of 1-[2-(2,4-dichlorophenyl)propyl]-1H-1,2,4-triazole; mp. 79.5° C.

Workup

  1. temperatureat reflux
  2. temperatureThe reaction mixture is cooled
  3. additionpoured onto water
  4. extractionthe product is extracted twice with 2,2'-oxybispropane
  5. washThe combined extracts are washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is crystallized from petroleumether
  10. filtrationThe product is filtered off
  11. customdried

Sources & evidence

ORD record
ord-0b9a6204b02246c6a8c2df7934ebf1bf
Source dataset
uspto-grants-1986_07
Patent number
US04598085

Reaction notes

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