Hydrochloric Acid → 3-[(Propane-1-sulfonyl)amino]benzoic acid

HRID 1261026Notes

Reaction equation

HRID 1261026 reaction equation
C([O:3][C:4](=[O:18])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][S:12]([CH2:15][CH2:16][CH3:17])(=[O:14])=[O:13])[CH:6]=1)C.[OH-].[Li+].O1CCCC1.Cl>O>[CH2:15]([S:12]([NH:11][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=1)[C:4]([OH:18])=[O:3])(=[O:13])=[O:14])[CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 58087920Ethyl 3-[(propane-1-sulfonyl)amino]benzoate

Product 1

HCID 162282623-[(Propane-1-sulfonyl)amino]benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 3-(propane-1-sulfonylamino)-benzoic acid ethyl ester (75, 1.60 g, 5.90 mmol) in water was added lithium hydroxide (1.0 g, 4.2 mmol) and tetrahydrofuran (20 mL). The reaction was stirred at room temperature overnight. The reaction mixture was acidified with 1 N HCl, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and washed with ethyl acetate to give the compound (76, 1.2 g, 84.5%) as white solid. MS (ESI) [M−H+]+=242.1.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. washwashed with ethyl acetate
  6. customto give the compound (76, 1.2 g, 84.5%) as white solid

Sources & evidence

ORD record
ord-1d6d7f11a3c642658c59d4e228935761
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

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