Water → N-(3,4-dichloro-5-isothiazolecarbonyl)-N-(4-chlorophenyl)-4-methoxybenzenesulfonamide

HRID 49406Notes

Reaction equation

HRID 49406 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1.[Cl:20][C:21]1[C:25]([Cl:26])=[C:24]([C:27](Cl)=[O:28])[S:23][N:22]=1.O>CN(C)C=O>[Cl:20][C:21]1[C:25]([Cl:26])=[C:24]([C:27]([N:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[O:28])[S:23][N:22]=1

Participants

5

Reactant 3

HCID 962WaterHCID 598671N-(4-Chlorophenyl)-4-methoxybenzenesulfonamideHCID 109768863,4-Dichloro-5-isothiazolecarbonyl chloride

Product 1

HCID 11408949N-(3,4-dichloro-5-isothiazolecarbonyl)-N-(4-chlorophenyl)-4-methoxybenzenesulfonamideYield 36.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of N-(4-chlorophenyl)-4-methoxybenzenesulfonamide (1.98 g) in unhydrous N,N-dimethylformamide (20 ml) 60% sodium hydride (0.24 g) was added at room temperature. After stirring the reaction mixture at the same temperature for 1 hour, a solution of 3,4-dichloro-5-isothiazolecarbonyl chloride (1.1 g) in unhydrous N,N-dimethylformamide (10 ml) was added thereto dropwise. After finishing the addition, the reaction mixture was stirred at room temperature for 18 hours and poured into water. The mixture was extracted with ethyl acetate and the organic phase was washed with water and dried with unhydrous sodium sulfate. The crude product obtained by distilling off the solvent under reduced pressure was recrystallized from ethanol to obtain N-(3,4-dichloro-5-isothiazolecarbonyl)-N-(4-chlorophenyl)-4-methoxybenzenesulfonamide (0.89 g). mp 154-158° C.

Workup

  1. additionthe addition
  2. stirringthe reaction mixture was stirred at room temperature for 18 hours
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic phase was washed with water
  5. dry with materialdried with unhydrous sodium sulfate
  6. customThe crude product obtained
  7. distillationby distilling off the solvent under reduced pressure
  8. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-3585ca59184a4e89bbba02979f2ff0d0
Source dataset
uspto-grants-2004_03
Patent number
US06706748B2

Reaction notes

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