تفاعل #2006462

ord-8b9092541a694e2f9f336c2762e30246

معادلة التفاعل

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
المردود 90.0%

المذيبات

ظروف التفاعل

درجة الحرارة
100°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

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

الإجراء التجريبي

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).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08168567B2uspto-grants-2012_05