Sulfuric Acid → 4-Amino-3-sulfamoylbenzoic acid

HRID 1066157Notes

Reaction equation

HRID 1066157 reaction equation
O.O=C1[NH:8][C:7]2[CH:9]=[CH:10][C:11]([C:13]([OH:15])=[O:14])=[CH:12][C:6]=2[S:5](=[O:17])(=[O:16])[NH:4]1.S(=O)(=O)(O)O.[OH-].[Na+]>O>[NH2:8][C:7]1[CH:9]=[CH:10][C:11]([C:13]([OH:15])=[O:14])=[CH:12][C:6]=1[S:5](=[O:17])(=[O:16])[NH2:4]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 702368523-Oxo-2,3-dihydro-4H-1,2,4-benzothiadiazine-7-carboxylic acid 1,1-dioxide monohydrate

Product 1

HCID 114016534-Amino-3-sulfamoylbenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 3-oxo-2,3-dihydro-4H-1,2,4-benzothiadiazine-7-carboxylic acid 1,1-dioxide monohydrate (10 g) in a mixture of concentrated sulfuric acid (150 mL) and water (150 mL) was refluxed until complete dissolution of the starting material (1-2 h). The resulting solution was placed on an ice bath and supplemented dropwise with a 20% aqueous solution of NaOH under stirring and cooling until pH 1-2. The precipitate was collected by filtration, washed with water and dried (yield: 6.6 g); m.p.: 214-219° C.

Workup

  1. temperaturewas refluxed until complete dissolution of the starting material (1-2 h)
  2. customThe resulting solution was placed on an ice bath
  3. temperaturecooling until pH 1-2
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. customdried (yield: 6.6 g)

Sources & evidence

ORD record
ord-27a9caaf5c9e42fd90493585425d5a4a
Source dataset
uspto-grants-2001_06
Patent number
US06242443B1

Reaction notes

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