Citric Acid → 2-Methanesulfonyl-6-trifluoromethyl-isonicotinic acid

HRID 878213Notes

Reaction equation

HRID 878213 reaction equation
O[O:2][S:3]([O-:5])=O.[K+].O.CS[C:10]1[CH:11]=[C:12]([CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[N:18]=1)[C:13]([OH:15])=[O:14].[C:23](O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.CCOC(C)=O>[CH3:23][S:3]([C:10]1[CH:11]=[C:12]([CH:16]=[C:17]([C:19]([F:22])([F:20])[F:21])[N:18]=1)[C:13]([OH:15])=[O:14])(=[O:5])=[O:2]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 70663362HCID 70663362, compound

Product 1

HCID 670547082-Methanesulfonyl-6-trifluoromethyl-isonicotinic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To an ice-cold suspension of Oxone® (525 mg, 854 μmol, CAS RN 10058-23-8) in methanol (0.6 mL) and water (0.6 mL) was added dropwise a solution of 2-methylsulfanyl-6-trifluoromethyl-isonicotinic acid (0.09 g, 341 μmol) in methanol (1.2 mL) and the reaction mixture was stirred in an ice-bath for 2 hours. After stirring at room temperature for another 4.5 hours the reaction mixture was poured on 10% aqueous citric acid solution and EtOAc and the layers were separated. The aqueous layer was extracted twice with EtOAc and the organic layers were washed with water, 10% aqueous Na2S2O3 solution and brine, dried over MgSO4, filtered, and evaporated. Colorless solid (0.106 g; 98%). MS (ESI): m/z=267.99 [M−H]−. This material was used in the next step without further purification.

Workup

  1. stirringAfter stirring at room temperature for another 4.5 hours the reaction mixture
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted twice with EtOAc
  4. washthe organic layers were washed with water, 10% aqueous Na2S2O3 solution and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThis material was used in the next step without further purification

Sources & evidence

ORD record
ord-0e08727fbb1a4e6399d59e45d71d7ce3
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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