Hydrochloric Acid → 2,4-Dichloro-5-[[(2-fluorophenyl)amino]sulfonyl]benzoic acid

HRID 400525Notes

Reaction equation

HRID 400525 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[C:10]([S:14]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])(=[O:16])=[O:15])=[CH:9][C:3]=1[C:4]([O:6]CC)=[O:5].C(O)C.[OH-].[Na+].Cl>O>[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[C:10]([S:14]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])(=[O:16])=[O:15])=[CH:9][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 66675729HCID 66675729, compound

Product 1

HCID 23243772,4-Dichloro-5-[[(2-fluorophenyl)amino]sulfonyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the product of Step A was added ethanol (8 mL) followed by a solution of NaOH (0.378 g, 9.45 mmol) in water (8 mL). The reaction was stirred at ambient temperature for 45 minutes. To the mixture was added 1 N HCl (23 mL), and the mixture was stirred overnight. The solids were collected by filtration, washed with water (1×5 mL), and dried by vacuum filtration to give 2,4-dichloro-5-{[(2-fluorophenyl)amino]sulfonyl}benzoic acid: 1H NMR (400 MHz, DMSO-d6) δ ppm 13.50 (bs, 1H), 10.30 (bs, 1H), 8.22 (s, 1H), 8.04 (s, 1H), 7.28-7.11 (m, 4H); MS (ESI) m/z 362.3 (M−H)−.

Workup

  1. stirringthe mixture was stirred overnight
  2. filtrationThe solids were collected by filtration
  3. washwashed with water (1×5 mL)
  4. customdried by vacuum filtration

Sources & evidence

ORD record
ord-7a8fead3480e4722a68645089870897c
Source dataset
uspto-grants-2014_06
Patent number
US08741899B2

Reaction notes

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