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

HRID 1098364Notes

Reaction equation

HRID 1098364 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.[OH-].[K+].O.Cl>O1CCCC1>[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 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 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 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 6-chloro-2-fluoro-3-(propane-1-sulfonylamino)-benzoic acid benzyl ester (49, 6.00 g, 15.6 mmol) in tetrahydrofuran (100 mL) was added 1.0 M aqueous potassium hydroxide (100 mL). 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, filtrated and concentrated to give a white solid 115 (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. filtrationfiltrated
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-85e140eb75c1467db73aadfc58582615
Source dataset
uspto-grants-2012_03
Patent number
US08143271B2

Reaction notes

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