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Methanol → 3-(3-p-Tolylsulfamoyl-phenyl)-acrylic acid

HRID 226126
Notes
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Reaction equation

HRID 226126 reaction equation
C[O:2][C:3](=[O:23])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([S:12](=[O:22])(=[O:21])[NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[CH:7]=1.CO>>[C:17]1([CH3:20])[CH:16]=[CH:15][C:14]([NH:13][S:12]([C:8]2[CH:7]=[C:6]([CH:5]=[CH:4][C:3]([OH:23])=[O:2])[CH:11]=[CH:10][CH:9]=2)(=[O:21])=[O:22])=[CH:19][CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 887MethanolHCID 670195113-(3-p-Tolylsulfamoyl-phenyl)-acrylic acid methyl ester

Product 1

HCID 670195353-(3-p-Tolylsulfamoyl-phenyl)-acrylic acidYield 87.5%

Procedure

To a suspension of 3-(3-p-tolylsulfamoyl-phenyl)-acrylic acid methyl ester (4d) (0.89 g, 2.70 mmol) in methanol (12 ml) 1N NaOH solution (8.10 ml, 8.10 mmol) was added and the resultant mixture was stirred at ambient temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. The aqueous layer was acidified with 2N HCl solution 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 (0.75 g, 87%).

Workup

  1. additionwas added
  2. custom
The reaction mixture was partitioned between ethyl acetate and water
  • filtrationThe precipitated solid was filtered
  • washwashed with water
  • dry with materialdried in desiccator over P2O5
  • Sources & evidence

    ORD record
    ord-6f5204a1c77148f0ae7e413ea2139ebf
    Source dataset
    uspto-grants-2009_07
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US07557140B2

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes