Ethanol → HCID 23676785, compound

HRID 1492714Notes

Reaction equation

HRID 1492714 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[S:13]([O-:16])([OH:15])=[O:14].[Na+:17].C(O)C>O>[F:10][C:9]([F:12])([F:11])[C:5]1[CH:6]=[C:7]([Cl:8])[C:2]([S:13]([O-:16])(=[O:15])=[O:14])=[N:3][CH:4]=1.[Na+:17]

Participants

5

Reactant 3

HCID 702EthanolHCID 1122342,3-Dichloro-5-(trifluoromethyl)pyridineHCID 23665763Sodium Bisulfite

Product 1

HCID 23676785HCID 23676785, compoundYield 103%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a flask, 2,3-dichloro-5-(trifluoromethyl)pyridine (10.8 g, 50 mmol), sodium hydrogen sulfite (20.8 g, 200 mmol), ethanol (100 ml) and water (100 ml) were charged and heated under reflux for 41 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 metanol phase was filtered and evaporated to dryness to obtain quantitatively sodium 5-trifluoromethyl-3-chloropyridine-2-sulfonate (14.6 g). Decomposition point, 322°-334° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 41 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 metanol phase was filtered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-79589bcbec3b448fae5f5ebd2a08972f
Source dataset
uspto-grants-1994_12
Patent number
US05374732

Reaction notes

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