Реакция #684980

ord-9cd5eba7b93f40d7b1939722ff445764

Уравнение реакции

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
Выход 120.2%

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

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

Методика

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.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US07897560B2uspto-grants-2011_03