Methanol → HCID 67019613, compound

HRID 2180387Notes

Reaction equation

HRID 2180387 reaction equation
C[O:2][C:3](=[O:24])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([S:12](=[O:23])(=[O:22])[NH:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:7]=1.CO>>[CH2:14]([NH:13][S:12]([C:8]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]([OH:24])=[O:2])[CH:11]=[CH:10][CH:9]=1)(=[O:23])=[O:22])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 67019615HCID 67019615, compound

Product 1

HCID 67019613HCID 67019613, compoundYield 78%

Procedure

To a suspension of 3-(3-phenethylsulfamoyl-phenyl)-acrylic acid methyl ester (4h) (0.20 g, 0.58 mmol) in methanol (3.0 ml) 1N NaOH solution (1.75 ml, 1.75 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 2N HCl solution and extracted with ethyl acetate. The organic layer was washed successively with water, saturated NaCl, and dried (Na2SO4). The solvent was removed and the residue was washed with ether to give the title compound as a white solid (0.15 g, 77%).

Workup

  1. additionwas added
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed successively with water, saturated NaCl
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was removed
  7. washthe residue was washed with ether

Sources & evidence

ORD record
ord-e3e26a8a14fb4db09a82fbf6f40c1f83
Source dataset
uspto-grants-2005_05
Patent number
US06888027B2

Reaction notes

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