Ethanol → HCID 23676787, compound

HRID 1492713Notes

Reaction equation

HRID 1492713 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[S:12]([O-:15])([OH:14])=[O:13].[Na+:16].C(O)C>O>[F:9][C:8]([F:11])([F:10])[C:7]1[C:2]([S:12]([O-:15])(=[O:14])=[O:13])=[N:3][CH:4]=[CH:5][CH:6]=1.[Na+:16]

Participants

5

Reactant 3

HCID 702EthanolHCID 5898332-Chloro-3-(trifluoromethyl)pyridineHCID 23665763Sodium Bisulfite

Product 1

HCID 23676787HCID 23676787, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a flask, 2-chloro-3-(trifluoromethyl)pyridine (20.0 g, 110 mmol) , sodium hydrogen sulfite (46 g, 442 mmol), ethanol (200 ml) and water (200 ml) were charged and heated under reflux for 138 hours. After evaporating off the solvent from the reaction mixture, conc. hydrochloric acid was added to the residue and then evaporated to dryness. This residue was extracted with methanol, and the methanol phase was filtered and evaporated to dryness to obtain sodium 3-(trifluoromethyl)pyridine-2-sulfonate (18.6 g). Yield, 68%.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 138 hours
  3. customAfter evaporating off the solvent from the reaction mixture, conc. hydrochloric acid
  4. additionwas added to the residue
  5. customevaporated to dryness
  6. extractionThis residue was extracted with methanol
  7. filtrationthe methanol phase was filtered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-d10075efa5fb4aa4b671c2089826fabd
Source dataset
uspto-grants-1994_12
Patent number
US05374732

Reaction notes

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