Methanol → 3-{3-[(E)-2-Phenylethenesulfonylamino]phenyl}acrylic acid

HRID 226160Notes

Reaction equation

HRID 226160 reaction equation
C[O:2][C:3](=[O:24])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][S:13](/[CH:16]=[CH:17]/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:15])=[O:14])[CH:7]=1.CO>>[C:18]1(/[CH:17]=[CH:16]/[S:13]([NH:12][C:8]2[CH:7]=[C:6]([CH:5]=[CH:4][C:3]([OH:24])=[O:2])[CH:11]=[CH:10][CH:9]=2)(=[O:15])=[O:14])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 670195993-{3-[(E)-2-Phenylethenesulfonylamino]phenyl}acrylic acid methyl ester

Product 1

HCID 7501113-{3-[(E)-2-Phenylethenesulfonylamino]phenyl}acrylic acid

Procedure

To a suspension of 3-{3-[(E)-2-phenylethenesulfonylamino]phenyl}acrylic acid methyl ester (25a) (0.30 g, 0.87 mmol) in methanol (4 ml) 1N NaOH solution (2.62 ml, 2.62 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 extracted with ethyl acetate. The extract was washed with saturated NaCl and dried (Na2SO4). The solvent was evaporated and the residue was dried in desiccator over P2O5. The title compound was obtained as a white solid (0.26 g, 90%). 1H NMR (DMSO-d6, HMDSO) δ: 6.41 (1H, d, J=16.0 Hz); 7.12-7.51 (9H, m); 7.55-7.81 (3H, m); 10.16 (1H, br s), 12.32 (1H, br s).

Workup

  1. additionwas added
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated NaCl
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was evaporated
  7. dry with materialthe residue was dried in desiccator over P2O5

Sources & evidence

ORD record
ord-0c44df6a409a40659a970cd26d00a821
Source dataset
uspto-grants-2009_07
Patent number
US07557140B2

Reaction notes

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