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

HRID 1690012Notes

Reaction equation

HRID 1690012 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 (13, 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. The reaction was poured into water, acidified to pH 2 with 1 N hydrochloric acid and extracted with ethyl acetate. The organic portion was dried over anhydrous sodium sulfate, filtered and the filtrate concentrated under vacuum to provide the desired compound as a white solid (14, 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-74aaae88ea1646f89e3cec8006de4f9d
Source dataset
uspto-grants-2012_04
Patent number
US08153641B2

Reaction notes

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