1H-1,2,4-Triazole → HCID 50940483, compound

HRID 587828Notes

Reaction equation

HRID 587828 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]([F:18])([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])[CH:6]=[C:5]([CH3:19])[C:4]=1[NH:20][C:21](=[O:32])[C:22]1[CH:27]=[CH:26][C:25](F)=[C:24]([N+:29]([O-:31])=[O:30])[CH:23]=1)[CH3:2].[NH:33]1[CH:37]=[N:36][CH:35]=[N:34]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]([F:18])([C:10]([F:12])([F:11])[F:13])[C:14]([F:15])([F:17])[F:16])[CH:6]=[C:5]([CH3:19])[C:4]=1[NH:20][C:21](=[O:32])[C:22]1[CH:27]=[CH:26][C:25]([N:33]2[CH:37]=[N:36][CH:35]=[N:34]2)=[C:24]([N+:29]([O-:31])=[O:30])[CH:23]=1)[CH3:2]

Participants

6

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 86666613HCID 86666613, compound

Product 1

HCID 50940483HCID 50940483, compoundYield 84.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

N-[2-Ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl]-4-fluoro-3-nitrobenzamide (1.5 g, see WO 2005/073165) and 1H-1,2,4-triazole (0.24 g) were dissolved in N,N-dimethylformamide (15 ml). To the solution, potassium carbonate (0.88 g) was added and the mixture was stirred under heating at 70° C. for 3 hours. After cooling to room temperature, the reaction solution was diluted with water and extracted twice with ethyl acetate. The organic phases were combined, washed with water and dried over magnesium sulfate. After filtering off the drying agent, the solvent was distilled off under reduced pressure to obtain a crude product. The resulting crude product was purified by column chromatography to obtain N-[2ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl]-3-nitro-4-(1H-1,2,4-triazol-1-yl)benzamide (1.4 g, yield 80%).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted twice with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtering off the drying agent
  6. distillationthe solvent was distilled off under reduced pressure
  7. customto obtain a crude product
  8. customThe resulting crude product was purified by column chromatography

Sources & evidence

ORD record
ord-f53019bcea184a2a82785593ef1c873d
Source dataset
uspto-grants-2016_01
Patent number
US09227923B2

Reaction notes

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