Ethanol → HCID 23676783, compound

HRID 1492712Notes

Reaction equation

HRID 1492712 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[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:5]1[CH:6]=[CH:7][C:2]([S:12]([O-:15])(=[O:14])=[O:13])=[N:3][CH:4]=1.[Na+:16]

Participants

5

Reactant 3

HCID 702EthanolHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 23665763Sodium Bisulfite

Product 1

HCID 23676783HCID 23676783, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a flask, 2-chloro-5-(trifluoromethyl)pyridine (54.5 g, 0.3 mol), sodium hydrogen sulfite (125 g, 1.2 mol), ethanol (600 ml) and water (600 ml) were charged and heated under reflux for 198 hours. After evaporating off the solvent, to the solid residue, conc. hydrochloric acid was added. The mixture was evaporated to dryness. The residue was extracted with methanol and filtrated. The filtrate was evaporated to dryness to obtain sodium 5-(trifluoromethyl)pyridine-2-sulfonate (64.0 g). Yield, 86%. Decomposition point, 356°-370° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 198 hours
  3. customAfter evaporating off the solvent
  4. additionto the solid residue, conc. hydrochloric acid was added
  5. customThe mixture was evaporated to dryness
  6. extractionThe residue was extracted with methanol
  7. filtrationfiltrated
  8. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-dbe6bbea85a04be2b6aca60899dcb366
Source dataset
uspto-grants-1994_12
Patent number
US05374732

Reaction notes

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