Water → HCID 14763077, compound

HRID 326690Notes

Reaction equation

HRID 326690 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:9][C:4]=2[O:3][CH2:2]1.[OH-].[Na+].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]=[O:25])=[CH:19][CH:18]=1.O>CC(C)=O>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH:13][S:10]([C:8]2[CH:7]=[CH:6][C:5]3[O:1][CH2:2][O:3][C:4]=3[CH:9]=2)(=[O:12])=[O:11])=[O:25])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 76934-Chlorophenyl IsocyanateHCID 14798Sodium HydroxideHCID 1928092H-1,3-Benzodioxole-5-sulfonamide

Product 1

HCID 14763077HCID 14763077, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 26.9 g of 1,3-benzodioxole-5-sulfonamide in 100 ml of acetone was added 150 ml of a 1N sodium hydroxide solution. A solution of 26.4 g of 4-chlorophenylisocyanate in 85 ml of acetone was added to the reaction mixture with stirring. After stirring at room temperature for 18 hours, the reaction mixture was filtered and 150 ml of 1N hydrochloric acid were added to the filtrate, thereby providing a precipitate. One liter of water was added, and the solid was recovered by filtration to provide the desired title product in 75% yield.

Workup

  1. stirringAfter stirring at room temperature for 18 hours
  2. filtrationthe reaction mixture was filtered
  3. addition150 ml of 1N hydrochloric acid were added to the filtrate
  4. customproviding a precipitate
  5. filtrationthe solid was recovered by filtration

Sources & evidence

ORD record
ord-18ce0e9fa57b487aaf2669b75358c73a
Source dataset
uspto-grants-1993_12
Patent number
US05270329

Reaction notes

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