Sodium Hydroxide → HCID 67019595, compound

HRID 226165Notes

Reaction equation

HRID 226165 reaction equation
C[O:2][C:3](=[O:22])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12](=[O:21])(=[O:20])[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[Na+]>CO>[C:14]1([NH:13][S:12]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH:5]=[CH:4][C:3]([OH:22])=[O:2])(=[O:21])=[O:20])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67019617HCID 67019617, compound

Product 1

HCID 67019595HCID 67019595, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(2-phenylsulfamoyl-phenyl)-acrylic acid methyl ester (34a) (0.30 g, 0.94 mmol) was dissolved in methanol (4 ml), 1N NaOH solution (2.82 ml, 2.82 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 10% HCl solution and stirred at ambient temperature for 1 hour. The precipitated solid was filtered, washed with water and dried in desiccator over P2O5. The title compound (0.2 g, 70%) was obtained as a white solid. 1H NMR (DMSO-d6, HMDSO), δ: 6.40 (1H, d, J=16.0 Hz); 6.93-7.32 (5H, m); 7.45-8.00 (5H, m); 8.47 (1H, d, J=16.0 Hz); 10.59 (1H, br s).

Workup

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

Sources & evidence

ORD record
ord-3992c113912348798711b73d194efa92
Source dataset
uspto-grants-2009_07
Patent number
US07557140B2

Reaction notes

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