Methanol → HCID 67019640, compound

HRID 351037Notes

Reaction equation

HRID 351037 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][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=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:23])=[O:2])[CH:11]=[CH:10][CH:9]=1)(=[O:22])=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 67019556HCID 67019556, compound

Product 1

HCID 67019640HCID 67019640, compoundYield 81%

Procedure

To a suspension of 3-(3-benzylsulfamoyl-phenyl)-acrylic acid methyl ester (4g) (0.29 g, 0.87 mmol) in methanol (4.5 ml) 1N NaOH solution (2.60 ml, 2.60 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 (0.22 g, 81%). 1H NMR (DMSO-d6, HMDSO), δ: 4.05 (2H, d, J=6.4 Hz); 6.60 (1H, d, J=16.0 Hz); 7.27 (4H, s), 7.52–8.09 (6H, m); 8.20 (1H, t, J=6.4 Hz); 12.58 (1H, br s).

Workup

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

Sources & evidence

ORD record
ord-7ee148d2ef9c429fa5f923e0946662b6
Source dataset
uspto-grants-2007_02
Patent number
US07183298B2

Reaction notes

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