Реакция #2006462

ord-8b9092541a694e2f9f336c2762e30246

Уравнение реакции

CCOC(C)=O
ethyl acetate
[H-].[Na+]
sodium hydride
Cc1cc(O)c(C)cc1N
2,5-dimethyl-4-hydroxyaniline
CC(C)(C)c1nsc(Cl)n1
3-(tert-butyl)-5-chloro-1,2,4-thiadiazole
Cc1cc(Oc2nc(C(C)(C)C)ns2)c(C)cc1N
4-[(3-(tert-Butyl)-1,2,4-thiadiazol-5-yl)oxy]-2,5-dimethylaniline
Выход 90.0%

Растворители

Условия реакции

Температура
100°CELSIUS
Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    workup.ADDITIONare added
  2. 2
    Температураcooled down to AT
  3. 3
    Экстракцияthe solution is extracted three times with water
  4. 4
    Сушкаdried over MgSO4
  5. 5
    Другоеthe solvent is removed under vacuum (1.46 g, 94% purity, 90% yield, log P (pH 2.3)=3.29)

Методика

754 mg (5.50 mmol) of 2,5-dimethyl-4-hydroxyaniline are dissolved in 5 ml of N,N-dimethylformamide and slowly treated with 242 mg (6.05 mmol) of sodium hydride. The reaction mixture is stirred for 15 min, before 972 mg (5.50 mmol) of 3-(tert-butyl)-5-chloro-1,2,4-thiadiazole are added. Subsequently, the reaction mixture is heated at 100° C. for 1 h and then cooled down to AT. After addition of 20 ml of ethyl acetate, the solution is extracted three times with water and dried over MgSO4, and the solvent is removed under vacuum (1.46 g, 94% purity, 90% yield, log P (pH 2.3)=3.29).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US08168567B2uspto-grants-2012_05