Chlorosulfonic acid → HCID 86646364, compound

HRID 2092947Notes

Reaction equation

HRID 2092947 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[CH3:19])[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]([CH3:19])=[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 68440948HCID 68440948, compound

Product 1

HCID 86646364HCID 86646364, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

In a 25-ml eggplant flask provided with a magnetic stirrer were placed 5.83 g (50 mol) of chlorosulfonic acid and then 2.49 g (9.73 mmol) of 4-(5-amino-3-trifluoromethyl-1H-1,2,4-triazol-1-yl)-1,3-dimethylbenzene. The mixture was stirred at 60° 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 3.3 g of a crystal. Yield: 96%

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-72a0e516a27341308cc5b41d40d0fb0d
Source dataset
uspto-grants-2013_05
Patent number
US08440838B2

Reaction notes

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