Anthranilic Acid → HCID 69747102, compound

HRID 1061860Notes

Reaction equation

HRID 1061860 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+].[C:17]1(C)[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.[CH4:28].Cl>O>[C:19]1([CH3:28])[C:20]([S:23]([C:6]2[CH:5]=[C:3]([NH2:4])[C:2](=[CH:8][CH:7]=2)[C:1]([OH:10])=[O:9])(=[O:24])=[O:25])=[CH:21][CH:22]=[CH:17][CH:18]=1

Participants

7

Reactant 5

HCID 227Anthranilic AcidHCID 297MethaneHCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 10340Sodium Carbonate

Product 1

HCID 69747102HCID 69747102, compoundYield 110.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

13.7 g (0.1 mol) of anthranilic acid was added in three portions to the warmed solution of 26.0 g of sodium carbonate in 150 ml of water, 23.0 g (0.12 mol) of p-toluenesulfonyl chloride was added to the solution in 5 portions over a period of 20 minutes. Maintained the reaction mixture at 60-70° C. for additional 0.5 h, and rised to 85° C., 1.0 g of Norit was added cautiously and the solution was fitered. The filtrate was cooled and acidified with dilute HCl, the product was isolated by filtration and washed with dilute hydrochloric acid and then water. After recrystallized from 95% ethanol there was obtained the title compound (20.0 g) as white crystal, yield 68.7%, m.p. 229-232° C.

Workup

  1. additionwas added to the solution in 5 portions over a period of 20 minutes
  2. customrised to 85° C.
  3. temperatureThe filtrate was cooled
  4. customthe product was isolated by filtration
  5. washwashed with dilute hydrochloric acid
  6. customAfter recrystallized from 95% ethanol

Sources & evidence

ORD record
ord-305f34d0431c41d5b6a1bacfb22171b7
Source dataset
uspto-grants-2005_11
Patent number
US06960611B2

Reaction notes

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