Реакция #1884962

ord-898e242162d8486fb5e3eaee4ead7238

Уравнение реакции

CC(C)(C)N
tert-Butylamine
O=S(=O)(Cl)CCCCl
3-Chloropropanesulfonyl chloride
CC(C)(C)NS(=O)(=O)CCCCl
product
Выход 99.0%
CC(C)(C)NS(=O)(=O)CCCCl
N-tert-Butyl-(3-chloro)propylsulfonamide
Выход 99.0%

Реагенты

Нет

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    ТемператураThe solution was cooled to −200C
  2. 2
    ФильтрацияThe mixture was filtered
  3. 3
    Концентрированиеthe filtrate was concentrated in vacuo
  4. 4
    workup.DISSOLUTIONThe residue was dissolved in CH2Cl2 (2.0 L)
  5. 5
    ПромывкаThe resulting solution was washed with 1 N HCl (1.0 L), water (1.0 L), brine (1.0 L)
  6. 6
    Сушкаdried over Na2SO4
  7. 7
    ФильтрацияIt was filtered
  8. 8
    Концентрированиеconcentrated in vacuo
  9. 9
    Другоеto give a slightly yellow solid, which
  10. 10
    Другоеwas crystallized from hexane

Методика

tert-Butylamine (3.0 mol, 315.3 mL) was dissolved in THF (2.5 L). The solution was cooled to −200C. 3-Chloropropanesulfonyl chloride (1.5 mol, 182.4 mL) was added slowly. The reaction mixture was allowed to warm to rt and stirred for 24 h. The mixture was filtered, and the filtrate was concentrated in vacuo. The residue was dissolved in CH2Cl2 (2.0 L). The resulting solution was washed with 1 N HCl (1.0 L), water (1.0 L), brine (1.0 L) and dried over Na2SO4. It was filtered and concentrated in vacuo to give a slightly yellow solid, which was crystallized from hexane to afford the product as a white solid (316.0 g, 99%).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US08343477B2uspto-grants-2013_01