Anthranilic Acid → Benzoic acid, 2-(((4-methylphenyl)sulfonyl)amino)-

HRID 990108

Reaction equation

HRID 990108 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[C:7]([OH:16])(=[O:15])[C:8]1[C:9](=[CH:11][CH:12]=[CH:13][CH:14]=1)[NH2:10].[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.Cl>O>[CH3:27][C:17]1[CH:22]=[CH:21][C:20]([S:23]([NH:10][C:9]2[C:8](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]([OH:16])=[O:15])(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 227Anthranilic AcidHCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 10340Sodium Carbonate

Product 1

HCID 22763Benzoic acid, 2-(((4-methylphenyl)sulfonyl)amino)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3.45 g (25 mmol) of sodium carbonate and 1.0 g (7.3 mmol) of anthranilic acid in 50 ml of water at 60° was treated with 2.09 g (10.95 mmol) of p-toluenesulfonyl chloride and held at 70° for 30 min. The reaction mixture was cooled to ambient temperature and acidified with 10% HCl. After standing for 18 hr the product was collected by filtration, washed with water and dried to give N-4-methylphenylsulfonylanthranilic acid as a solid, mp 226-229°.

Workup

  1. waitAfter standing for 18 hr
  2. filtrationthe product was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-8ea78ecd93754de4ba3e88942421c7d1
Source dataset
uspto-grants-2002_10
Patent number
US06458845B1

Linked notes

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