Reacción #684980

ord-9cd5eba7b93f40d7b1939722ff445764

Ecuación de reacción

O=C1CCC(=O)N1Br
N-bromosuccinimide
CCCCCCCCCCCC(=O)NS(=O)(=O)c1ccc(C)cc1
N-dodecanoyl-4-methylbenzenesulfonamide
CCOC(C)=O
Ethyl acetate
CCCCCCC
heptane
CCCCCCCCCCCC(=O)NS(=O)(=O)c1ccc(CBr)cc1
4-bromomethyl-N-(dodecanoyl)benzenesulfonamide
Rendimiento 120.2%

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    TemperaturaThe reaction mixture was heated for 1 h to 80° C
  2. 2
    TemperaturaThe reaction mixture was heated another 2 h to 80° C
  3. 3
    OtroThe solid was removed by filtration
  4. 4
    OtroThe solvent was removed from the filtrate

Procedimiento

At 80° C., N-bromosuccinimide (1.43 g, 8.06 mmol) and dibenzoylperoxide (62 mg, 0.25 mmol) were added successively to a solution of N-dodecanoyl-4-methylbenzenesulfonamide (3 g, 8.48 mmol) in tetrachloromethane (75 ml). The reaction mixture was heated for 1 h to 80° C. Another portion of dibenzoylperoxide (100 mg, 0.41 mmol) was added. The reaction mixture was heated another 2 h to 80° C. It was cooled to room temperature and left for 16 h. Ethyl acetate (100 ml) and heptane (100 ml) were added. The solid was removed by filtration. The solvent was removed from the filtrate to give 4.19 g of crude 4-bromomethyl-N-(dodecanoyl)benzenesulfonamide, which was used for the next step, without further purification.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07897560B2uspto-grants-2011_03