Ethanol → 3-{[(3-Fluorophenyl)amino]sulfonyl}benzoic acid

HRID 1951490Notes

Reaction equation

HRID 1951490 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][S:9]([C:12]2[CH:13]=[C:14]([CH:20]=[CH:21][CH:22]=2)[C:15]([O:17]CC)=[O:16])(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.C(O)C.[OH-].[Na+]>O>[F:1][C:2]1[CH:3]=[C:4]([NH:8][S:9]([C:12]2[CH:13]=[C:14]([CH:20]=[CH:21][CH:22]=2)[C:15]([OH:17])=[O:16])(=[O:10])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 66676257Ethyl 3-{[(3-fluorophenyl)amino]sulfonyl}benzoate

Product 1

HCID 7665363-{[(3-Fluorophenyl)amino]sulfonyl}benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the product of Step A was added ethanol (6.4 mL) followed by a solution of NaOH (0.483 g, 12.1 mmol) in water (6.4 mL). The reaction was stirred at ambient temperature for 1 hour. To the mixture was added 1 NHCl (22.8 mL), and the mixture stirred at ambient temperature overnight. The solids were collected by filtration, washed with water (2×4 mL) and dried in a vacuum oven at 45° C. overnights to give 3-{[(3-fluorophenyl)amino]sulfonyl}benzoic acid: 1H NMR (400 MHz, DMSO-d6) δ ppm 13.51 (bs, 1H), 10.68 (bs, 1H), 8.30 (t, J=1.8, 1H), 8.14 (dt, J=7.7, 1.4, 1H), 7.99 (ddd, J=7.8, 2.0, 1.1, 1H), 7.70 (t, J=7.8, 1H), 7.27 (m, 1H), 6.94-6.82 (m, 3H); MS (ESI) m/z 294 (M−H)−.

Workup

  1. additionTo the mixture was added 1 NHCl (22.8 mL)
  2. stirringthe mixture stirred at ambient temperature overnight
  3. filtrationThe solids were collected by filtration
  4. washwashed with water (2×4 mL)
  5. customdried in a vacuum oven at 45° C. overnights

Sources & evidence

ORD record
ord-69274046df0848aa9d79d783c2a64056
Source dataset
uspto-grants-2013_03
Patent number
US08404719B2

Reaction notes

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