1H-1,2,4-Triazole → HCID 70222247, compound

HRID 581997Notes

Reaction equation

HRID 581997 reaction equation
[Cl:1][C:2]1[C:11]([CH:12](Cl)[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[NH:24]1[CH:28]=[N:27][CH:26]=[N:25]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[C:11]([CH:12]([N:24]2[CH:28]=[N:27][CH:26]=[N:25]2)[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 70221442HCID 70221442, compound

Product 1

HCID 70222247HCID 70222247, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of intermediate 6 (8.4 g), 1,2,4-triazole (4.89 g) and potassium carbonate (9.78 g) in acetonitrile (300 ml) was stirred and refluxed for 12 hours. The solvent was evaporated and the residue was partitioned between CH2Cl2 and water. The separated organic layer was dried over MgSO4, filtered and the filtrate evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH/NH4OH 98.5/1.5/0.1). The pure fractions were collected and the solvent evaporated. The residue was crystallized from diisopropyl ether/petrol ether, yielding 1.51 g (32%) (±)-5-chloro-6-[1H-1,2,4-triazol-1-yl[3-(trifluoromethyl)phenyl]-methyl]quinoline (intermediate 7; mp. 144.5° C.). In a similar manner, there were prepared: (±)-8-methyl-6-[1H-1,2,4-triazol-1-yl[3-(trifluoromethyl)phenyl]methyl]quinoline (intermediate 8; mp. 108.9° C.) and (±)-8-fluoro-6-[1H-1,2,4-triazol-1-yl[3-(trifluoromethyl) phenyl]methyl]quinoline (intermediate 9; mp. 146.6° C.).

Workup

  1. temperaturerefluxed for 12 hours
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between CH2Cl2 and water
  4. dry with materialThe separated organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customthe filtrate evaporated
  7. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH/NH4OH 98.5/1.5/0.1)
  8. customThe pure fractions were collected
  9. customthe solvent evaporated
  10. customThe residue was crystallized from diisopropyl ether/petrol ether

Sources & evidence

ORD record
ord-482fe16042d64d45a0dee772623b23e3
Source dataset
uspto-grants-1999_07
Patent number
US05922734

Reaction notes

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