1H-1,2,4-Triazole → HCID 23315389, compound

HRID 745281Notes

Reaction equation

HRID 745281 reaction equation
[H-].[Na+].CS(O[CH2:8][CH:9]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)(=O)=O.[NH:26]1[CH:30]=[N:29][CH:28]=[N:27]1>CN(C)C=O>[ClH:18].[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([CH:9]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[CH2:8][N:26]2[CH:30]=[N:29][CH:28]=[N:27]2)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 23315392HCID 23315392, compound

Product 1

HCID 23315389HCID 23315389, compoundYield 32.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a stirred mixture of 3.8 parts of a sodium hydride dispersion 78% and 90 parts of N,N-dimethylformamide is added dropwise a solution of 21 parts of 2,4-bis(4-chlorophenyl)butyl methanesulfonate in 45 parts of N,N-dimethylformamide. After stirring for 15 minutes at room temperature, there is added a solution of 7.6 parts of 1H-1,2,4-triazole in 45 parts of N,N-dimethylformamide. The whole is heated slowly to 100° C. and stirring is continued for 2 hours at 100° C. The reaction mixture is poured onto water and the product is extracted with 1,1'-oxybisethane. The extract is washed with water, dried, filtered and evaporated. The oily residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (97.5:2.5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The oily residue is converted into the hydrochoride salt in 2,2'-oxybispropane. The salt is filtered off and crystallized from a mixture of methanol and 2,2'-oxybispropane, yielding 7 parts (32.5%) of 1-[2,4-bis(4-chlorophenyl)butyl]-1H-1,2,4-triazole hydrochloride; mp. 173.4° C.

Workup

  1. temperatureThe whole is heated slowly to 100° C.
  2. stirringstirring
  3. waitis continued for 2 hours at 100° C
  4. additionThe reaction mixture is poured onto water
  5. extractionthe product is extracted with 1,1'-oxybisethane
  6. washThe extract is washed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe oily residue is purified by column-chromatography over silica gel using
  11. additiona mixture of trichloromethane and methanol (97.5:2.5 by volume) as eluent
  12. customThe pure fractions are collected
  13. customthe eluent is evaporated
  14. filtrationThe salt is filtered off
  15. customcrystallized from a mixture of methanol and 2,2'-oxybispropane

Sources & evidence

ORD record
ord-37a371d00de64580806f24d28c1212a5
Source dataset
uspto-grants-1986_07
Patent number
US04598085

Reaction notes

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