1H-1,2,4-Triazole → HCID 49824866, compound

HRID 582000Notes

Reaction equation

HRID 582000 reaction equation
Cl[CH:2]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1)[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH:7]=[CH:6]2.[NH:24]1[CH:28]=[N:27][CH:26]=[N:25]1.C(=O)([O-])[O-].[K+].[K+]>CC#N>[N:24]1([CH:2]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][CH:12]=2)[NH:9][C:8](=[O:13])[CH:7]=[CH:6]3)[CH:28]=[N:27][CH:26]=[N:25]1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 53916288HCID 53916288, compound

Product 1

HCID 49824866HCID 49824866, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of intermediate 30 (0.846 g), 1,2,4-triazole (0.346 g) and potassium carbonate (0.7 g) in CH3CN (30 ml) was stirred and refluxed for 2 hours. The solvent was evaporated and the residue was taken up in water and extracted with CH2Cl2. The organic layer was dried MgSO4, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH/NH4OH 98/2/0.1) and the solvent of the desired fraction was evaporated, yielding 0.25 g (27%) of (±)-6-[1H-1,2,4-triazol-1-yl[3-(trifluoromethyl)phenyl]methyl]-2(1H)-quinolinone (compound 3).

Workup

  1. temperaturerefluxed for 2 hours
  2. customThe solvent was evaporated
  3. extractionextracted with CH2Cl2
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH/NH4OH 98/2/0.1)
  7. customthe solvent of the desired fraction was evaporated

Sources & evidence

ORD record
ord-85bf1a8ec83a48abb9218784470afa80
Source dataset
uspto-grants-1999_07
Patent number
US05922734

Reaction notes

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