1H-1,2,4-Triazole → HCID 22161906, compound

HRID 1088730Notes

Reaction equation

HRID 1088730 reaction equation
Br[C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[S:21]([C:24]([F:27])([F:26])[F:25])(=[O:23])=[O:22].[NH:28]1[CH:32]=[N:31][CH:30]=[N:29]1.[H-].[Na+]>O1CCOCC1>[C:19]([C:4]1[C:3]([S:21]([C:24]([F:27])([F:26])[F:25])(=[O:23])=[O:22])=[C:2]([N:28]2[CH:32]=[N:31][CH:30]=[N:29]2)[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=1)#[N:20]

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 167270545-Bromo-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfonylpyrazole

Product 1

HCID 22161906HCID 22161906, compoundYield 15.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5-bromo-3-cyano-1-(2,6-dichloro -4-trifluoromethylphenyl)-4-trifluoromethylsulphonylpyrazole (2.0 g) in dioxan (30 ml) was added 1,2, 4-triazole (0.74 g), and the mixture heated under reflux overnight. After cooling to ambient temperature, sodium hydride (0.125 g) was added and the mixture heated under reflux for 2 days. The solvent was evaporated in vacuo and the residue dissolved in dichloromethane (50 ml) and washed with water (50 ml). The aqueous layer was re-extracted with dichloromethane (50 ml) and the combined organics dried over anhydrous magnesium sulphate, then evaporated in vacuo to give a yellow oil. Purification by chromatography on silica, eluting with dichloromethane/hexane (1:1) gave 3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)- 5-(1,2,4-triazol-1-yl)-4-trifluoromethylsulphonylpyrazole (0.3 g) as a white solid, m.p. 172.3°-173.7° C.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux overnight
  3. temperaturethe mixture heated
  4. temperatureunder reflux for 2 days
  5. customThe solvent was evaporated in vacuo
  6. dissolutionthe residue dissolved in dichloromethane (50 ml)
  7. washwashed with water (50 ml)
  8. extractionThe aqueous layer was re-extracted with dichloromethane (50 ml)
  9. dry with materialthe combined organics dried over anhydrous magnesium sulphate
  10. customevaporated in vacuo
  11. customto give a yellow oil
  12. customPurification by chromatography on silica
  13. washeluting with dichloromethane/hexane (1:1)

Sources & evidence

ORD record
ord-6364447a69dc4db3bf82184af779e672
Source dataset
uspto-grants-1990_10
Patent number
US04963575

Reaction notes

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