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634189-17-6

Benzamide, 5-chloro-N-(2,4-difluorophenyl)-2-hydroxy- synthesis

4synthesis methods
-

Yield:634189-17-6 12%

Reaction Conditions:

with pyridine;phosphorus trichloride in toluene; for 12 h;Inert atmosphere;Reflux;

Steps:

59 4.1.1 Procedure A

General procedure: The salicylic acid (1.2 equiv) was added to a mixture of toluene (0.3 M), aniline (1.0 equiv), phosphorus trichloride (1.1 equiv), and pyridine (0.05 equiv) in a Radley’s Carousel reaction tube (modified from Itai et al.20). The mixture was refluxed under nitrogen for 12 h then cooled to room temperature. Aqueous sodium bicarbonate was added dropwise to attain pH 6-7. The resultant mixture was extracted with EtOAc. The organic extracts were combined, dried (MgSO4), and concentrated under vacuum. After chromatography (1:10 EtOAc:Hex) compounds were recrystallized (EtOAc/Hex).

References:

Lee, Ill-Young;Gruber, Todd D.;Samuels, Amanda;Yun, Minhan;Nam, Bora;Kang, Minseo;Crowley, Kathryn;Winterroth, Benjamin;Boshoff, Helena I.;Barry III, Clifton E. [Bioorganic and Medicinal Chemistry,2013,vol. 21,# 1,p. 114 - 126]