Chlorosulfonic acid → HCID 86646363, compound

HRID 2092946Notes

Reaction equation

HRID 2092946 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[NH2:6][C:7]1[N:11]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=2[F:19])[N:10]=[C:9]([C:20]([F:23])([F:22])[F:21])[N:8]=1>C(OCC)(=O)C>[NH2:6][C:7]1[N:11]([C:12]2[C:13]([F:19])=[CH:14][C:15]([CH3:18])=[C:16]([S:2]([Cl:1])(=[O:5])=[O:3])[CH:17]=2)[N:10]=[C:9]([C:20]([F:23])([F:22])[F:21])[N:8]=1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 68438670HCID 68438670, compound

Product 1

HCID 86646363HCID 86646363, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

In a 25-ml eggplant flask provided with a magnetic stirrer were placed 2.91 g (25 mmol) of chlorosulfonic acid and then 1.3 g (5 mmol) of 4-(5-amino-3-trifluoromethyl-1H-1,2,4-triazol-1-yl)-3-fluorotoluene. The mixture was stirred at 80° C. for 3 hours and cooled to room temperature. The mixture was added onto ice in small portions, and 30 ml of ethyl acetate was added 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, dried over anhydrous sodium sulfate, and subjected to vacuum distillation to distill off ethyl acetate, to obtain a title compound as 1.66 g of a crystal. Yield: 93%

Workup

  1. customIn a 25-ml eggplant flask provided with a magnetic stirrer
  2. temperaturecooled to room temperature
  3. additionwas added
  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. distillationsubjected to vacuum distillation
  10. distillationto distill off ethyl acetate

Sources & evidence

ORD record
ord-29481b61c6bf4a70860e4e7e4232d277
Source dataset
uspto-grants-2013_05
Patent number
US08440838B2

Reaction notes

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