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

HRID 351030Notes

Reaction equation

HRID 351030 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-042e572164214f4ea9bb08c242c4536f
Source dataset
uspto-grants-2007_02
Patent number
US07183298B2

Reaction notes

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