Anthranilic Acid → 2-[(Sulfomethyl)amino]benzoic acid

HRID 269372Notes

Reaction equation

HRID 269372 reaction equation
[CH2:1]=O.[S:3](=[O:6])([OH:5])[O-:4].[Na+].[C:8]([OH:17])(=[O:16])[C:9]1[C:10](=[CH:12][CH:13]=[CH:14][CH:15]=1)[NH2:11].S(=O)(O)[O-].Cl>O>[S:3]([CH2:1][NH:11][C:10]1[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=1[C:8]([OH:17])=[O:16])([OH:5])(=[O:4])=[O:6]

Participants

7

Reactant 5

HCID 227Anthranilic AcidHCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 104748BisulfiteHCID 23665763Sodium Bisulfite

Product 1

HCID 595474082-[(Sulfomethyl)amino]benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

Formaldehyde solution (37%, 31.6 g, 0.4 mol) and sodium bisulfite (38 g, 0.37 mol) were dissolved in water (200 ml) and the stirred mixture warmed to 60° C. Anthranilic acid (50 g, 0.37 mol) was dissolved in water (200 ml) at pH 7, and this solution was added to the bisulfite adduct solution, maintaining the temperature at 60-70° C. for 2 hours. The reaction mixture was allowed to cool slowly before hydrochloric acid was added to precipitate the product as a white solid. The product was collected by filtration and washed with saturated sodium chloride solution and then acetone. The dried product (34 g) contained 22.5% salt.

Workup

  1. temperaturemaintaining the temperature at 60-70° C. for 2 hours
  2. additionwas added
  3. customto precipitate the product as a white solid
  4. filtrationThe product was collected by filtration
  5. washwashed with saturated sodium chloride solution

Sources & evidence

ORD record
ord-fb925813f70c496393fe8b07f2d71847
Source dataset
uspto-grants-2008_11
Patent number
US07446184B2

Reaction notes

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