Water → HCID 178460705, compound

HRID 1657385Notes

Reaction equation

HRID 1657385 reaction equation
[S:1]([C:5]1[CH:11]=[C:10]([S:12][CH:13]([CH3:15])[CH3:14])[C:9]([Cl:16])=[CH:8][C:6]=1[NH2:7])(=[O:4])(=[O:3])[NH2:2].[Cl:17][CH2:18][C:19](Cl)=O.C([O-])(=O)C.[K+].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][CH:13]([CH3:14])[CH3:15])[C:9]([Cl:16])=[CH:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 517044Potassium AcetateHCID 21533306HCID 21533306, compound

Product 1

HCID 178460705HCID 178460705, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-sulfamoyl-4-isopropylthio-5-chloroaniline (0.02 mole) and chloroacetyl chloride (0.022 mole) in dioxane (75 ml.) is heated under reflux for 24 hours. The solution then is concentrated to dryness in vacuo, the residue dissolved in ethanol (60 ml.) and heated under reflux with potassium acetate (0.022 mole) and water (10 ml.) for 2 hours. The alcohol is removed in vacuo and the solution then acidified with hydrochloric acid. The precipitated product is recrystallized from a mixture of methanol and water to provide 3-chloromethyl-6-chloro-7-isopropylthio-1,2,4-benzothiadiazine-1,1-dioxide, m.p. 248°-250° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 24 hours
  3. concentrationThe solution then is concentrated to dryness in vacuo
  4. dissolutionthe residue dissolved in ethanol (60 ml.)
  5. temperatureheated
  6. customThe alcohol is removed in vacuo
  7. customThe precipitated product is recrystallized from a mixture of methanol and water

Sources & evidence

ORD record
ord-0c675b95bcfc461aa72c7f3f64098570
Source dataset
uspto-grants-1976_06
Patent number
US03960854

Reaction notes

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