Hydrochloric Acid → HCID 42633943, compound

HRID 241330Notes

Reaction equation

HRID 241330 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]2[CH:13]=[N:12][C:11]([C:14]([F:17])([F:16])[F:15])=[N:10]2)=[CH:4][C:3]=1[S:18](Cl)(=O)=O.C(O)C.Cl.O>[Zn].C(OCC)(=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]2[CH:13]=[N:12][C:11]([C:14]([F:15])([F:16])[F:17])=[N:10]2)=[CH:4][C:3]=1[SH:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 42633764HCID 42633764, compound

Product 1

HCID 42633943HCID 42633943, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In a 50-ml eggplant flask provided with a magnetic stirrer was placed 3.44 g (9.6 mmol) of 2,4-dimethyl-5-(3-trifluoromethyl-1H-1,2,4-triazol-1-yl)benzenesulfonyl chloride, followed by addition of 3.14 g (48 mmol) of zinc, 16 ml of ethanol and 8 ml (80 mmol) of 35% hydrochloric acid. The mixture was stirred at room temperature for 30 minutes and then refluxed with heating, for 4 hours. The mixture was cooled to room temperature. Thereto were added 50 ml of water and 50 ml of ethyl acetate to give rise to phase separation. The aqueous phase was extracted with 50 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 a title compound as 2.25 g of a crystal. Yield: 86%

Workup

  1. customIn a 50-ml eggplant flask provided with a magnetic stirrer
  2. temperaturerefluxed
  3. temperaturewith heating, for 4 hours
  4. temperatureThe mixture was cooled to room temperature
  5. customto give rise
  6. customto phase separation
  7. extractionThe aqueous phase was extracted with 50 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-3bd48c1fcf6a4edaac1328b5af4f0445
Source dataset
uspto-grants-2014_02
Patent number
US08648207B2

Reaction notes

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