Water → 3-Oxo-2,3-dihydro-4H-1,2,4-benzothiadiazine-7-carboxylic acid 1,1-dioxide monohydrate

HRID 1066156Notes

Reaction equation

HRID 1066156 reaction equation
[CH3:1][C:2]1[CH:14]=[CH:13][C:5]2[NH:6][C:7](=[O:12])[NH:8][S:9](=[O:11])(=[O:10])[C:4]=2[CH:3]=1.[OH-:15].[Na+].[Mn]([O-])(=O)(=O)=O.[K+].[OH2:23]>>[OH2:10].[O:12]=[C:7]1[NH:6][C:5]2[CH:13]=[CH:14][C:2]([C:1]([OH:23])=[O:15])=[CH:3][C:4]=2[S:9](=[O:11])(=[O:10])[NH:8]1

Participants

5

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 100818972H-1,2,4-Benzothiadiazin-3(4H)-one, 7-methyl-, 1,1-dioxide

Product 1

HCID 702368523-Oxo-2,3-dihydro-4H-1,2,4-benzothiadiazine-7-carboxylic acid 1,1-dioxide monohydrate

Conditions

Temperature
70 °C

Procedure

7-Methyl-3-oxo-2,3-dihydro-4H-1,2,4-benzothiadiazine 1,1-dioxide (20 g) was suspended in hot water (2000 mL) and supplemented dropwise with a 10% aqueous solution of NaOH until complete dissolution. Potassium permanganate (60 g) was added portionwise and the reaction mixture was stirred for 3 h at 70° C. After cooling, the insoluble material was removed by filtration and the purple filtrate was treated with sodium hydrogen sulfite until complete discolouration of the excess of permanganate. The solution was treated with charcoal, filtered, and the filtrate was adjusted to pH 0 with 12N HCl. The resulting suspension was placed at +4° C. during 2 h and the crystalline precipitate was collected by filtration, washed with water and dried (yield: 14.5 g); m.p.: 305-308° C.

Workup

  1. temperatureAfter cooling
  2. customthe insoluble material was removed by filtration
  3. additionthe purple filtrate was treated with sodium hydrogen sulfite until complete discolouration of the excess of permanganate
  4. additionThe solution was treated with charcoal
  5. filtrationfiltered
  6. waitThe resulting suspension was placed at +4° C. during 2 h
  7. filtrationthe crystalline precipitate was collected by filtration
  8. washwashed with water
  9. customdried (yield: 14.5 g)

Sources & evidence

ORD record
ord-cd044a37076446eb93997208ffdaa446
Source dataset
uspto-grants-2001_06
Patent number
US06242443B1

Reaction notes

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