Chloroacetyl chloride → 3-Chloromethyl-5-bromo-7-sulfamoyl-1,2,4-benzothiadiazine-1,1-dioxide

HRID 918186Notes

Reaction equation

HRID 918186 reaction equation
[S:1]([C:5]1[CH:11]=[C:10]([S:12](=[O:15])(=[O:14])[NH2:13])[CH:9]=[C:8]([Br:16])[C:6]=1[NH2:7])(=[O:4])(=[O:3])[NH2:2].[Cl:17][CH2:18][C:19](Cl)=O>O1CCOCC1>[Cl:17][CH2:18][C:19]1[NH:2][S:1](=[O:3])(=[O:4])[C:5]2[CH:11]=[C:10]([S:12](=[O:14])(=[O:15])[NH2:13])[CH:9]=[C:8]([Br:16])[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 22323981HCID 22323981, compound

Product 1

HCID 1785146823-Chloromethyl-5-bromo-7-sulfamoyl-1,2,4-benzothiadiazine-1,1-dioxide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2,4-disulfamoyl-6-bromoaniline (0.015 mole) and chloroacetyl chloride (0.016 mole) in 50 ml. of dioxane or other inert organic solvent is heated under reflux conditions for about 24 hours and then concentrated to dryness. The residue is dissolved in concentrated sulfuric acid (5 ml. acid/gram), heated in a steam bath at 60°-70° C. for three hours then poured onto ice. The product, 3-chloromethyl-5-bromo-7-sulfamoyl-1,2,4-benzothiadiazine-1,1-dioxide, is purified by recrystallization from a mixture of acetone-alcohol-water.

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe residue is dissolved in concentrated sulfuric acid (5 ml. acid/gram)
  3. temperatureheated in a steam bath at 60°-70° C. for three hours
  4. additionthen poured onto ice
  5. customThe product, 3-chloromethyl-5-bromo-7-sulfamoyl-1,2,4-benzothiadiazine-1,1-dioxide, is purified by recrystallization from a mixture of acetone-alcohol-water

Sources & evidence

ORD record
ord-0bb190d64ad84bdc9af6f241939eecf0
Source dataset
uspto-grants-1976_07
Patent number
US03969518

Reaction notes

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