Hydrochloric Acid → 2-Chloro-4-fluoro-5-{[(2-fluorophenyl)amino]sulfonyl}benzoic acid

HRID 421763

Reaction equation

HRID 421763 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([F: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]([F: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 66675861Ethyl 2-chloro-4-fluoro-5-{[(2-fluorophenyl)amino]sulfonyl}benzoate

Product 1

HCID 666758672-Chloro-4-fluoro-5-{[(2-fluorophenyl)amino]sulfonyl}benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To ethyl 2-chloro-4-fluoro-5-{[(2-fluorophenyl)amino]sulfonyl}benzoate (1.45 g) was added ethanol (6.4 mL) followed by a solution of NaOH (0.398 g, 9.96 mmol) in water (6.4 mL). The reaction was stirred at ambient temperature for 1 hour. To the mixture was added 1 N HCl (22.8 mL), and the mixture was stirred for 30 minutes. The solids were collected by filtration, washed with water (2×4 mL), and dried in a vacuum oven at 45° C. for 2.5 days to give 2-chloro-4-fluoro-5-{[(2-fluorophenyl)amino]sulfonyl}benzoic acid: 1H NMR (400 MHz, DMSO-d6) δ ppm 13.89 (s, 1H), 10.67 (s, 1H), 8.09 (d, J=7.7, 1H), 7.88 (d, J=9.9, 1H), 7.32-7.11 (m, 4H); MS (ESI) m/z 346 (M−H)−.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. filtrationThe solids were collected by filtration
  3. washwashed with water (2×4 mL)
  4. customdried in a vacuum oven at 45° C. for 2.5 days

Sources & evidence

ORD record
ord-9e211be95c8b460796ee0b7ff5d6cfa5
Source dataset
uspto-grants-2012_01
Patent number
US08101614B2

Linked notes

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