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

HRID 382897

Reaction equation

HRID 382897 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].C(=O)([O-])[O-].[Na+].[Na+].[S:17](Cl)([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18]>O>[S:17]([NH:4][C:3]1[C:2](=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:1]([OH:10])=[O:9])([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 227Anthranilic AcidHCID 73974-Toluenesulfonyl chloride2×HCID 10340Sodium Carbonate

Product 1

HCID 22763Benzoic acid, 2-(((4-methylphenyl)sulfonyl)amino)-Yield 78.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
78 °C

Procedure

In a 1 L reaction flask equipped with a condenser, 34.25 g (0.25 mol) of anthranilic acid, 411 g of water and 63.59 g (0.6 mol) of sodium carbonate were heated. The resulting reaction solution was maintained at an inner temperature of 78° C. for 30 minutes and then cooled to 67° C., and 57.2 g (0.3 mol) of tosyl chloride was added in two portions. The reaction solution gradually generated heat upon addition of tosyl chloride and turned homogeneous at 78° C. The reaction solution was aged at 80° C. for 1 hour. Crystals started to separate out in the first ten or so minutes of the aging. The completion of the reaction was confirmed by liquid chromatography, and the reaction solution was carefully neutralized with concentrated hydrochloric acid and allowed to cool. The crystals were collected by filtration at room temperature and washed with 100 ml of dilute hydrochloric acid at pH 3 and with 125 ml of water. Recrystallization from 247 g of n-propanol afforded 56.97 g of tosylanthranilic acid in a 78.3% yield.

Workup

  1. customIn a 1 L reaction flask
  2. customequipped with a condenser
  3. customThe resulting reaction solution
  4. temperaturecooled to 67° C.
  5. customturned homogeneous at 78° C
  6. customto separate out in the first ten or so minutes of the aging
  7. temperatureto cool
  8. filtrationThe crystals were collected by filtration at room temperature
  9. washwashed with 100 ml of dilute hydrochloric acid at pH 3 and with 125 ml of water
  10. customRecrystallization from 247 g of n-propanol

Sources & evidence

ORD record
ord-72988cf95c4c414bb1dfbac05dffe9d8
Source dataset
uspto-grants-2001_10
Patent number
US06310249B1

Linked notes

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