Water → 5-Chloro-3-[(4-chloro-3-trifluoromethyl-benzenesulfonyl)-methoxymethyl-amino]-pyridine-2-carboxylic acid

HRID 1898056Notes

Reaction equation

HRID 1898056 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:15]2[C:16]([CH:22]=[O:23])=[N:17][CH:18]=[C:19]([Cl:21])[CH:20]=2)[CH2:12][O:13][CH3:14])(=[O:10])=[O:9])=[CH:4][C:3]=1[C:24]([F:27])([F:26])[F:25].CC(=C)C.Cl([O-])=[O:33].[Na+].O>C(O)(C)(C)C.CCOC(C)=O>[Cl:21][C:19]1[CH:20]=[C:15]([N:11]([S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:24]([F:26])([F:25])[F:27])[CH:4]=2)(=[O:10])=[O:9])[CH2:12][O:13][CH3:14])[C:16]([C:22]([OH:33])=[O:23])=[N:17][CH:18]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8255IsobutyleneHCID 23668197Sodium ChloriteHCID 579420984-chloro-N-(5-chloro-2-formyl-pyridin-3-yl)-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide

Product 1

HCID 579422305-Chloro-3-[(4-chloro-3-trifluoromethyl-benzenesulfonyl)-methoxymethyl-amino]-pyridine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-chloro-N-(5-chloro-2-formyl-pyridin-3-yl)-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide (590 mg, 1.33 mmol) in tert-butanol (26 mL) was added isobutylene (5 mL), sodium chlorite (751 mg, 6.66 mmol) sodium dihydrogen phosphate (919 mg, 6.66 mmol) and water (26 mL). After the solution was stirred at room temperature for 3 h, EtOAc (10 mL) was added and the layers were separated. The organic layer was washed with saturated sodium bicarbonate (2×10 mL) and brine (1×10 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo to yield 5-chloro-3-[(4-chloro-3-trifluoromethyl-benzenesulfonyl)-methoxymethyl-amino]-pyridine-2-carboxylic acid as a white solid.

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with saturated sodium bicarbonate (2×10 mL) and brine (1×10 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-35d3e808eb904432bbcb223f31987149
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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