Sodium Hydroxide → 3-(3-Phenylsulfamoylphenyl)acrylic acid

HRID 2180378Notes

Reaction equation

HRID 2180378 reaction equation
C[O:2][C:3](=[O:22])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([S:12](=[O:21])(=[O:20])[NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:7]=1.[OH-].[Na+]>CO>[C:14]1([NH:13][S:12]([C:8]2[CH:7]=[C:6]([CH:5]=[CH:4][C:3]([OH:22])=[O:2])[CH:11]=[CH:10][CH:9]=2)(=[O:21])=[O:20])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67019508Methyl 3-[3-(phenylsulfamoyl)phenyl]prop-2-enoate

Product 1

HCID 670195203-(3-Phenylsulfamoylphenyl)acrylic acidYield 82.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(3-Phenylsulfamoylphenyl)acrylic acid methyl ester (4a) (0.220 g, 0.69 mmol) was dissolved in methanol (3 ml), 1N NaOH (2.08 ml, 2.08 mmol) was added and the resultant solution was stirred at ambient temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. The aqueous layer was acidified with 10% HCl and stirred for 30 min. The precipitated solid was filtered, washed with water and dried in desiccator over P2O5 to give the title compound as a white solid (0.173 g, 82%).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. filtrationThe precipitated solid was filtered
  3. washwashed with water
  4. dry with materialdried in desiccator over P2O5

Sources & evidence

ORD record
ord-507f8ccaa4cd451b943be5687c1e843e
Source dataset
uspto-grants-2005_05
Patent number
US06888027B2

Reaction notes

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