Potassium Hydroxide → [4-(Pyridin-2-ylsulfamoyl)-phenyl]-acetic acid

HRID 858074Notes

Reaction equation

HRID 858074 reaction equation
C([O:3][C:4](=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12](=[O:21])(=[O:20])[NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[CH:8][CH:7]=1)C.[OH-].[K+]>C(O)C>[N:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[NH:13][S:12]([C:9]1[CH:10]=[CH:11][C:6]([CH2:5][C:4]([OH:22])=[O:3])=[CH:7][CH:8]=1)(=[O:20])=[O:21]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 58762849[4-(Pyridin-2-ylsulfamoyl)-phenyl]-acetic acid ethyl ester

Product 1

HCID 24267818[4-(Pyridin-2-ylsulfamoyl)-phenyl]-acetic acidYield 65.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of [4-(pyridin-2-ylsulfamoyl)-phenyl]-acetic acid ethyl ester (0.26 g, 0.813 mmol) in absolute ethanol (10 mL) was treated with a 1.0M ethanolic potassium hydroxide solution (2.0 mL, 2.0 mmol). The reaction mixture was heated to reflux under argon for 3.5 h. The reaction mixture was then concentrated in vacuo. The residue was dissolved in water and filtered through celite. The filtrate was acidified to pH=4.5 with a 1.0M aqueous hydrochloric acid solution. The resulting precipitate was collected by filtration, washed with water, and dried in vacuo to afford [4-(pyridin-2-ylsulfamoyl)-phenyl]-acetic acid (155 mg, 65%) as an off white solid; 1H NMR (DMSO-d6, 300 MHz) δH 12.26 (broad s, 1H), 7.96 (d, J=4.4 Hz, 1H), 7.77 (d, J=7.7 Hz, 2H), 7.80 (t, J=7.5 Hz, 1H), 7.37 (d, J=7.7 Hz, 2H), 7.13 (d, J=8.8 Hz, 1H), 6.82 (broad s, 1H), 3.62 (s, 2H); LRMS for C13H12N2O4S (M+H)+ at m/z=293.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux under argon for 3.5 h
  3. concentrationThe reaction mixture was then concentrated in vacuo
  4. dissolutionThe residue was dissolved in water
  5. filtrationfiltered through celite
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-1999cab57aa548be94fb6fc5cbb5e8d5
Source dataset
uspto-grants-2006_12
Patent number
US07148229B2

Reaction notes

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