Chloroacetyl chloride → HCID 178514674, compound

HRID 918187Notes

Reaction equation

HRID 918187 reaction equation
[S:1]([C:5]1[CH:11]=[C:10]([S:12](=[O:15])(=[O:14])[NH2:13])[C:9]([Br:16])=[CH:8][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])[C:9]([Br:16])=[CH:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 5177804-Amino-6-bromo-1,3-benzenedisulfonamide

Product 1

HCID 178514674HCID 178514674, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2,4-disulfamoyl-5-bromoaniline (0.02 mole) and chloroacetyl chloride (0.022 mole) in 75 ml. of dioxane is heated under reflux for about 24 hours and then concentrated to dryness. The residue is dissolved in ethanol and then heated on the steam bath in a mixture of 2.0 g. of potassium or sodium acetate and 50 ml. of water for two hours. The solution is cooled and the product separated by acidification with hydrochloric acid and purified by recrystallization from a mixture of ethanol and water.

Workup

  1. temperatureunder reflux for about 24 hours
  2. concentrationconcentrated to dryness
  3. dissolutionThe residue is dissolved in ethanol
  4. temperatureheated on the steam bath in a mixture of 2.0 g
  5. temperatureThe solution is cooled
  6. customthe product separated by acidification with hydrochloric acid
  7. custompurified by recrystallization from a mixture of ethanol and water

Sources & evidence

ORD record
ord-29a48bc9dea84cd8804df219eb6e4a9b
Source dataset
uspto-grants-1976_07
Patent number
US03969518

Reaction notes

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