Reacción #318317

ord-c4993c3210e545c4affc8802d81baeb4

Ecuación de reacción

O
water
O=C=Nc1ccc(Br)cc1
4-bromophenylisocyanate
COc1ccc(S(N)(=O)=O)cc1
4-methoxybenzenesulfonamide
[Na+].[OH-]
sodium hydroxide
COc1ccc(S(=O)(=O)NC(=O)Nc2ccc(Br)cc2)cc1
desired title product
Rendimiento 91.9%
COc1ccc(S(=O)(=O)NC(=O)Nc2ccc(Br)cc2)cc1
N-([(4-Bromophenyl)amino]carbonyl)-4-methoxybenzenesulfonamide
Rendimiento 91.9%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.STIRRINGAfter stirring at room temperature for three days
  2. 2
    Filtraciónthe reaction mixture was filtered
  3. 3
    workup.ADDITION55 ml of 1N hydrochloric acid were added to the filtrate
  4. 4
    Otroproviding a fine white precipitate
  5. 5
    Filtraciónthe solid was recovered by filtration

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04845128uspto-grants-1989_07