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Hydrochloric Acid → 3-(Propane-1-sulfonamido)benzoic acid

HRID 250570
Notes
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Reaction equation

HRID 250570 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

HCID 162282623-(Propane-1-sulfonamido)benzoic acid

Reagents, catalysts & solvents 1

HCID 962Water
Solvent

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-5940567bbd6c4ab6b536858ae5fb340d
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07863288B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes