Anthranilic Acid → 2-{4-[2-(4-Fluoro-phenyl)-ethylcarbamoyl]-benzenesulfonylamino}-benzoic acid

HRID 643999Notes

Reaction equation

HRID 643999 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=2)=[O:12])=[CH:4][CH:3]=1.[C:23]([OH:32])(=[O:31])[C:24]1[C:25](=[CH:27][CH:28]=[CH:29][CH:30]=1)[NH2:26].C(=O)(O)[O-].[Na+]>C1COCC1.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([NH:26][C:25]3[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=3[C:23]([OH:32])=[O:31])(=[O:21])=[O:20])=[CH:15][CH:14]=2)=[O:12])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 227Anthranilic AcidHCID 516892Sodium BicarbonateHCID 866098204-[2-(4-Fluoro-phenyl)-ethylcarbamoyl]-benzenesulfonyl chloride

Product 1

HCID 592632782-{4-[2-(4-Fluoro-phenyl)-ethylcarbamoyl]-benzenesulfonylamino}-benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the title B compound, 4-[2-(4-fluoro-phenyl)-ethylcarbamoyl]-benzene-sulfonyl chloride (171 mg, 0.5 mmol) in THF (2 mL) is added dropwise over 10 min to a solution of the anthranilic acid (68.6 mg, 0.5 mmol) in water (1 mL) containing sodium bicarbonate (126 mg, 1.5 mmol). After stirring for 30 min, the solvent is evaporated under a stream of nitrogen, and water (8 mL) is added. The mixture is stirred for a few min, then filtered. The filtrate is added dropwise to an excess of 1 N aqueous HCl to precipitate a light tan solid. The solid is collected by filtration, washed with water, and dried under vacuum to give 2-{4-[2-(4-fluoro-phenyl)-ethylcarbamoyl]-benzenesulfonylamino}-benzoic acid: m.p. 85-86° C.; ESI-MS 441 [M−1]−.

Workup

  1. customthe solvent is evaporated under a stream of nitrogen, and water (8 mL)
  2. additionis added
  3. stirringThe mixture is stirred for a few min
  4. filtrationfiltered
  5. additionThe filtrate is added dropwise to an excess of 1 N aqueous HCl
  6. customto precipitate a light tan solid
  7. filtrationThe solid is collected by filtration
  8. washwashed with water
  9. customdried under vacuum

Sources & evidence

ORD record
ord-e152f47385f74736a2803895ebc097b8
Source dataset
uspto-grants-2010_04
Patent number
US07700637B2

Reaction notes

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