Hydrochloric Acid → 4-chloro-N-(5-chloro-2-formyl-pyridin-3-yi)-3-trifluoromethyl-benzenesulfonamide

HRID 419123Notes

Reaction equation

HRID 419123 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)COC)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:24]([F:27])([F:26])[F:25].O.Cl>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:15]2[C:16]([CH:22]=[O:23])=[N:17][CH:18]=[C:19]([Cl:21])[CH:20]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:24]([F:25])([F:27])[F:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 579420984-chloro-N-(5-chloro-2-formyl-pyridin-3-yl)-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide

Product 1

HCID 579424914-chloro-N-(5-chloro-2-formyl-pyridin-3-yi)-3-trifluoromethyl-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
80 °C

Procedure

The unpurified aldehyde from the previous reaction was magnetically stirred in dioxane (20 mL), water (20 mL), and 4N HCl in dioxane (40 mL); and heated at 80° C. (oil bath) overnight. LCMS indicated complete reaction; the reaction was concentrated and the residue was neutralized (pH 6) with aqueous sodium bicarbonate and extracted with ethyl acetate (3×80 mL). The extracts were dried (Na2SO4), filtered, and purified by flash column chromatography on silica gel using ethyl acetate-hexane to provide 4-chloro-N-(5-chloro-2-formyl-pyridin-3-yl)-3-trifluoromethyl-benzenesulfonamide. MS: (M+H)/z=398.9.

Workup

  1. customreaction
  2. concentrationthe reaction was concentrated
  3. extractionextracted with ethyl acetate (3×80 mL)
  4. dry with materialThe extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. custompurified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-d528a6ae2a164718804d6fdff728c02c
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Reaction notes

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