Pyridine → HCID 11076432, compound

HRID 1379295Notes

Reaction equation

HRID 1379295 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9](Cl)(=[O:11])=[O:10].N1C=C[CH:18]=[CH:17][CH:16]=1.CC[O:23]CC>C(O)(C)C>[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([O:23][CH:17]([CH3:18])[CH3:16])(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 3283Diethyl EtherHCID 1366162-Trifluoromethylbenzenesulphonyl chloride

Product 1

HCID 11076432HCID 11076432, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

A solution of 400 grams (g) of 2-trifluoromethylbenzenesulfonyl chloride in 600 milliliters (mL) of isopropanol was cooled in an ice bath and treated with a solution of 180 mL of pyridine in 200 mL of isopropanol at a rate to keep the internal temperature <10° C. The mixture was maintained at 0°-5° C. for 24 hours, then treated with 1 liter (L) of ether. The slurry was filtered and the solvent removed from the filtrate in vacuo. To the filtrate was added 800 mL of ether and the resulting mixture was washed with 500 mL portions of 5% aqueous hydrochloric acid, water, saturated aqueous sodium bicarbonate, water, and then brine. The organic phase was dried through calcium sulfate and the solvent removed in vacuo to yield 306 g isopropyl 2-trifluoromethylbenzenesulfonate as an oil.

Workup

  1. customthe internal temperature <10° C
  2. temperatureThe mixture was maintained at 0°-5° C. for 24 hours
  3. filtrationThe slurry was filtered
  4. customthe solvent removed from the filtrate in vacuo
  5. additionTo the filtrate was added 800 mL of ether
  6. washthe resulting mixture was washed with 500 mL portions of 5% aqueous hydrochloric acid, water, saturated aqueous sodium bicarbonate, water
  7. dry with materialThe organic phase was dried through calcium sulfate
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-526c33a4e9eb4c15b880f3964bf88b79
Source dataset
uspto-grants-1997_09
Patent number
US05670691

Reaction notes

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