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

HRID 1964871Notes

Reaction equation

HRID 1964871 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-5a8541b306174265ac5e7fff383d8821
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

Loading…