Water → 2-[(3-Bromophenyl)sulfonyl]-5-(4-chlorophenyl)-4-[(1E)-3,3,3-trifluoroprop-1-en-1-yl]-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 714669Notes

Reaction equation

HRID 714669 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:14][C@H:15](O)[C:16]([F:19])([F:18])[F:17])[C:10](=[O:13])[NH:11][N:12]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Br:27][C:28]1[CH:29]=[C:30]([S:34](Cl)(=[O:36])=[O:35])[CH:31]=[CH:32][CH:33]=1.O>C(#N)C>[Br:27][C:28]1[CH:29]=[C:30]([S:34]([N:11]2[C:10](=[O:13])[N:9](/[CH:14]=[CH:15]/[C:16]([F:19])([F:18])[F:17])[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)=[N:12]2)(=[O:36])=[O:35])[CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 17943m-Bromobenzenesulphonyl chlorideHCID 595368365-(4-Chlorophenyl)-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 699402022-[(3-Bromophenyl)sulfonyl]-5-(4-chlorophenyl)-4-[(1E)-3,3,3-trifluoroprop-1-en-1-yl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

500 mg (1.63 mmol) of the compound from Example 5A were dissolved in 10 ml of acetonitrile, and 449 mg (3.25 mmol) of potassium carbonate and 415 mg (1.63 mmol) of 3-bromobenzenesulfonyl chloride were added. The mixture was heated under reflux for 2 h. For work-up, 10 ml of water were added and the mixture was extracted twice with in each case 15 ml of ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 8:1→5:1→1:1). This gave 285 mg (34% of theory) of the target compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 h
  3. extractionthe mixture was extracted twice with in each case 15 ml of ethyl acetate
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 8:1→5:1→1:1)

Sources & evidence

ORD record
ord-19ff9d4c50c8429e8836dc5a2becd0f2
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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