Potassium Hydroxide → HCID 22323981, compound

HRID 496146Notes

Reaction equation

HRID 496146 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](=[O:11])(=[O:10])[NH2:9])=[CH:4][C:3]=1[S:12]([NH2:15])(=[O:14])=[O:13].[Br:16]Br.[OH-].[K+]>CC(O)=O>[NH2:1][C:2]1[C:7]([Br:16])=[CH:6][C:5]([S:8](=[O:10])(=[O:11])[NH2:9])=[CH:4][C:3]=1[S:12]([NH2:15])(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 24408BromineHCID 130719484-Aminobenzene-1,3-disulfonamide

Product 1

HCID 22323981HCID 22323981, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
70 °C

Procedure

A stirred solution of 2-amino-5-sulfamoylbenzenesulfonamide (3.77 g; 15 mmol) in AcOH (50 ml) was added a solution of Br2 (0.78 ml; 15 mmol) in AcOH (10 ml). The reaction mixture was heated to 70° C. for 6 days, evaporated to dryness, resuspended in MeOH (85 ml) and added solid KOH (3.8 g; 68 mmol). The reaction mixture was heated to 60° C. for 2.5 h (hydrolysis of 3-methyl-, 3-bromomethyl-, 3-dibromomethyl and 3-tribromomethyl-1,2-dihydro-1,2,4-benzothiadiazine isomers formed in situ), filtered, neutralized and evaporated to dryness. Column chromatography gave 3.1 g (63%) product.

Workup

  1. customevaporated to dryness
  2. temperatureThe reaction mixture was heated to 60° C. for 2.5 h
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-5feb0e5752524fdd884913da979f2f2e
Source dataset
uspto-grants-2005_09
Patent number
US06943159B1

Reaction notes

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