Water → N-([(4-Bromophenyl)amino]carbonyl)-4-methoxybenzenesulfonamide

HRID 231135

Reaction equation

HRID 231135 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH2:12])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[OH-].[Na+].[Br:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]=[C:23]=[O:24])=[CH:18][CH:17]=1.O>CC(C)=O>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]([NH:12][S:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)(=[O:11])=[O:10])=[O:24])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 707894-MethoxybenzenesulfonamideHCID 756094-Bromophenyl isocyanate

Product 1

HCID 14480021N-([(4-Bromophenyl)amino]carbonyl)-4-methoxybenzenesulfonamideYield 91.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 9.97 g of 4-methoxybenzenesulfonamide in 54 ml of acetone were added 54 ml of a 1N sodium hydroxide solution. With stirring, a solution of 11.55 g of 4-bromophenylisocyanate in 50 ml of acetone was added. After stirring at room temperature for three days, the reaction mixture was filtered and 55 ml of 1N hydrochloric acid were added to the filtrate providing a fine white precipitate. Two hundred milliliters of water were added, and the solid was recovered by filtration to provide 18.85 g of the desired title product.

Workup

  1. stirringAfter stirring at room temperature for three days
  2. filtrationthe reaction mixture was filtered
  3. addition55 ml of 1N hydrochloric acid were added to the filtrate
  4. customproviding a fine white precipitate
  5. filtrationthe solid was recovered by filtration

Sources & evidence

ORD record
ord-c4993c3210e545c4affc8802d81baeb4
Source dataset
uspto-grants-1989_07
Patent number
US04845128

Linked notes

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