Hydrochloric Acid → 6-Chloro-2-fluoro-3-(propane-1-sulfonamido)benzoic acid

HRID 1397843Notes

Reaction equation

HRID 1397843 reaction equation
C([O:8][C:9](=[O:25])[C:10]1[C:15]([Cl:16])=[CH:14][CH:13]=[C:12]([NH:17][S:18]([CH2:21][CH2:22][CH3:23])(=[O:20])=[O:19])[C:11]=1[F:24])C1C=CC=CC=1.O.Cl>O1CCCC1.[OH-].[K+]>[Cl:16][C:15]1[C:10]([C:9]([OH:25])=[O:8])=[C:11]([F:24])[C:12]([NH:17][S:18]([CH2:21][CH2:22][CH3:23])(=[O:19])=[O:20])=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 580867966-Chloro-2-fluoro-(propane-1-sulfonylamino)-benzoic acid benzyl ester

Product 1

HCID 580875006-Chloro-2-fluoro-3-(propane-1-sulfonamido)benzoic acidYield 85.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14797Potassium HydroxideSolvent

Procedure

To 6-chloro-2-fluoro-3-(propane-1-sulfonylamino)-benzoic acid benzyl ester (17, 6.00 g, 15.6 mmol) in 100 mL of tetrahydrofuran, 100 mL of 1.0 M aqueous potassium hydroxide was added. The reaction was heated to reflux overnight, then poured into water, acidified to pH 2 with 1 N aqueous hydrochloric acid and extracted with ethyl acetate. The organic portion was dried over anhydrous sodium sulfate, filtered and the filtrate concentrated under vacuum to give the desired compound as a white solid (18, 3.95 g, 85.8%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic portion was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-0541496e5e9a4e5cb13bbca72fd7bf48
Source dataset
uspto-grants-2014_12
Patent number
US08901301B2

Reaction notes

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