Chlorosulfonic acid → HCID 42633764, compound

HRID 2092948Notes

Reaction equation

HRID 2092948 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH:17]=[N:16][C:15]([C:18]([F:21])([F:20])[F:19])=[N:14]2)=[C:9]([CH3:22])[CH:8]=1>C(OCC)(=O)C>[CH3:6][C:7]1[CH:8]=[C:9]([CH3:22])[C:10]([N:13]2[CH:17]=[N:16][C:15]([C:18]([F:20])([F:21])[F:19])=[N:14]2)=[CH:11][C:12]=1[S:2]([Cl:1])(=[O:5])=[O:3]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 42633763HCID 42633763, compound

Product 1

HCID 42633764HCID 42633764, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

In a 25-ml eggplant flask provided with a magnetic stirrer were placed 2.5 g (22 mol) of chlorosulfonic acid and then 1.8 g (7.4 mmol) of 1,3-dimethyl-4-(3-trifluoromethyl-1H-1,2,4-triazol-1-yl)benzene. The mixture was stirred at 70° C. for 2 hours. The mixture was cooled to room temperature and then added onto ice in small portions. Thereto was added 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 a saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate. Then, vacuum distillation was conducted to distill off ethyl acetate to obtain a title compound as 2.5 g of brown oil. Yield: 99%

Workup

  1. customIn a 25-ml eggplant flask provided with a magnetic stirrer
  2. temperatureThe mixture was cooled to room temperature
  3. additionadded onto ice in small portions
  4. customto give rise
  5. customto phase separation
  6. extractionThe aqueous phase was extracted with 30 ml of ethyl acetate
  7. washThe ethyl acetate phase was washed with a saturated aqueous sodium chloride solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThen, vacuum distillation
  10. distillationto distill off ethyl acetate

Sources & evidence

ORD record
ord-a00cc8b01ee4477ab134f0c7b1ab7bc3
Source dataset
uspto-grants-2013_05
Patent number
US08440838B2

Reaction notes

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