Methanol → 3-[3-(Naphthalen-2-ylsulfamoyl)-phenyl]-acrylic acid

HRID 226154Notes

Reaction equation

HRID 226154 reaction equation
C[O:2][C:3](=[O:26])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([S:12](=[O:25])(=[O:24])[NH:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[CH:7]=1.CO>>[CH:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:22]=[CH:23][C:14]=1[NH:13][S:12]([C:8]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]([OH:26])=[O:2])[CH:11]=[CH:10][CH:9]=1)(=[O:24])=[O:25]

Participants

3

Reactant 2

HCID 887MethanolHCID 670194963-[3-(Naphthalen-2-ylsulfamoyl)-phenyl]-acrylic acid methyl ester

Product 1

HCID 670195903-[3-(Naphthalen-2-ylsulfamoyl)-phenyl]-acrylic acid

Procedure

To a suspension of 3-[3-(naphthalen-2-ylsulfamoyl)-phenyl]-acrylic acid methyl ester (14e) (0.25 g, 0.68 mmol) in methanol (3.5 ml) 2N NaOH solution (1.0 ml, 2.0 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. The title compound was obtained as a white solid (0.21 g, 87%). 1H NMR (DMSO-d6, HMDSO), δ: 6.56 (1H, d, J=16.0 Hz), 7.21-8.01 (11H, m); 8.12 (1H, s); 10.56 (1H, br s); 12.54 (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-f02c59eb7aec4a6cb5f206e62211be7f
Source dataset
uspto-grants-2009_07
Patent number
US07557140B2

Reaction notes

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