1H-1,2,4-Triazole → 1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-ol

HRID 745279Notes

Reaction equation

HRID 745279 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[N:6][CH:5]=[N:4]1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH2:17]Cl)[OH:16])=[CH:11][CH:10]=1>CN(C)C=O>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([OH:16])[CH2:17][N:3]2[CH:7]=[N:6][CH:5]=[N:4]2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 1108344-Chloro-alpha-(chloromethyl)benzenemethanol

Product 1

HCID 5580621-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-olYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 3.4 parts of a sodium hydride dispersion 78% in 90 parts of N,N-dimethylformamide are added portionwise, during a 5 minutes-period, 6.9 parts of 1H-1,2,4-triazole. After stirring for 10 minutes at room temperature, there are added 19.1 parts of 4-chloro-α-(chloromethyl)benzenemethanol. The whole is stirred and refluxed for 8 hours. The reaction mixture is cooled and poured onto water. The product is extracted with dichloromethane. The extract is washed with water, dried, filtered and evaporated. The residue is triturated in 2,2'-oxybispropane. The product is filtered off and crystallized from methylbenzene, yielding 17.3 parts (77%) of α-(4-chlorophenyl)-1H-1,2,4-triazole-1-ethanol; mp. 119° C.

Workup

  1. stirringThe whole is stirred
  2. temperaturerefluxed for 8 hours
  3. temperatureThe reaction mixture is cooled
  4. additionpoured onto water
  5. extractionThe product is extracted with dichloromethane
  6. washThe extract is washed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue is triturated in 2,2'-oxybispropane
  11. filtrationThe product is filtered off
  12. customcrystallized from methylbenzene

Sources & evidence

ORD record
ord-43b8f06b0bc44125a92bc2e0346d2550
Source dataset
uspto-grants-1986_07
Patent number
US04598085

Reaction notes

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