Hydrochloric Acid → HCID 68441156, compound

HRID 241328Notes

Reaction equation

HRID 241328 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:8]([F:18])=[CH:9][C:10]([CH3:17])=[C:11]([S:13](Cl)(=O)=O)[CH:12]=2)[N:5]=[C:4]([C:19]([F:22])([F:21])[F:20])[N:3]=1.C(O)C.Cl.O>[Zn].C(OCC)(=O)C>[NH2:1][C:2]1[N:6]([C:7]2[C:8]([F:18])=[CH:9][C:10]([CH3:17])=[C:11]([SH:13])[CH:12]=2)[N:5]=[C:4]([C:19]([F:22])([F:21])[F:20])[N:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 86646363HCID 86646363, compound

Product 1

HCID 68441156HCID 68441156, compoundYield 102.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

In a 25-ml eggplant flask provided with a magnetic stirrer was placed 1.83 g (5 mmol) of 5-(5-amino-3-trifluoromethyl-1H-1,2,4-triazol-1-yl)-4-fluoro-2-methylbenzenesulfonyl chloride, followed by addition of 1.6 g (25 mmol) of zinc, 10 ml of ethanol and 10 ml of (100 mmol) of 18% hydrochloric acid. The mixture was stirred at room temperature for 15 minutes. Then, the mixture was refluxed with heating until the zinc powder was dissolved completely. The mixture was cooled to room temperature. Thereto were added 30 ml of water and 30 ml of ethyl acetate to give rise to phase separation. The aqueous phase was extracted with 30 ml of ethyl acetate. The ethyl acetate phase was washed with water and then with a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. Vacuum distillation was conducted to distil off ethyl acetate to obtain 1.5 g of a crystal. Yield: 100%

Workup

  1. customIn a 25-ml eggplant flask provided with a magnetic stirrer
  2. temperatureThen, the mixture was refluxed
  3. dissolutionwas dissolved completely
  4. temperatureThe mixture was cooled to room temperature
  5. customto give rise
  6. customto phase separation
  7. extractionThe aqueous phase was extracted with 30 ml of ethyl acetate
  8. washThe ethyl acetate phase was washed with water
  9. dry with materialwith a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate
  10. distillationVacuum distillation
  11. customto distil off ethyl acetate

Sources & evidence

ORD record
ord-c96eb76cf41945828be6e88b6bd52912
Source dataset
uspto-grants-2014_02
Patent number
US08648207B2

Reaction notes

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