Potassium Carbonate → HCID 68440619, compound

HRID 241324Notes

Reaction equation

HRID 241324 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([C:7]([F:10])([F:9])[F:8])[N:3]=1.[F:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1F)[C:15]#[N:16].C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C.CN(C)C=O>[NH2:1][C:2]1[N:6]([C:19]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=2[F:11])[N:5]=[C:4]([C:7]([F:10])([F:9])[F:8])[N:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 5872033,4-DifluorobenzonitrileHCID 178508429HCID 178508429, compound

Product 1

HCID 68440619HCID 68440619, compoundYield 58.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
60 °C

Procedure

In a 50-ml eggplant flask provided with a magnetic stirrer were placed 3.04 g (20 mmol) of 5-amino-3-trifluoromethyl-1H-1,2,4-triazole, 3.06 g (22 mmol) of 3,4-difluorobenzonitrile, 2.76 g (20 mmol) of potassium carbonate and then 10 ml of N,N-dimethylformamide. The mixture was stirred at 60° C. for 6 hours. Thereto were added 50 ml of ethyl acetate and 50 ml of water to give rise to phase separation. The aqueous phase was extracted with 50 mol of ethyl acetate. The ethyl acetate phase was washed with water and then with a saturated aqueous sodium chloride solution. The ethyl acetate phase was dried over anhydrous sodium sulfate and then subjected to vacuum distillation to distil off ethyl acetate. To the residue was added 5 ml of toluene. The mixture was stirred with heating, cooled and then filtered to obtain 3.18 g of a crystal. Yield: 58.6%

Workup

  1. customIn a 50-ml eggplant flask provided with a magnetic stirrer
  2. customto give rise
  3. customto phase separation
  4. washThe ethyl acetate phase was washed with water
  5. dry with materialThe ethyl acetate phase was dried over anhydrous sodium sulfate
  6. distillationsubjected to vacuum distillation
  7. customto distil off ethyl acetate
  8. additionTo the residue was added 5 ml of toluene
  9. stirringThe mixture was stirred
  10. temperaturewith heating
  11. temperaturecooled
  12. filtrationfiltered

Sources & evidence

ORD record
ord-f68acf0cc5884635905ee93c22c96a1b
Source dataset
uspto-grants-2014_02
Patent number
US08648207B2

Reaction notes

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