反応 #82127

反応方程式

diphenylphosphorylazide

4-hexyloxybenzoic acid

triethylamine

4-(2-aminophenethyl)-2,6-di-tert-butylphenol

→

N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(4-hexyloxyphenyl)urea

収率 71.1%

溶媒

toluene

toluene

反応条件

後処理

1. 1
   温度to cool (under 0° C.)
2. 2
   温度The solution was warmed up to room temperature
3. 3
   workup.STIRRINGstirred overnight
4. 4
   workup.DISTILLATIONAfter distilling off
5. 5
   その他the solvent and purification of the residue
6. 6
   その他by a silica gel column chromatography, recrystallization from ethyl acetate/hexane

実験手順

A solution of diphenylphosphorylazide (0.93 g, 3.4 mmol), 4-hexyloxybenzoic acid (0.68 g, 3.1 mmol) and triethylamine (0.34 g, 3.4 mmol) in toluene (10 ml) was stirred at room temperature for 3.5 hrs and heated at about 90° C. for 2 hrs with stirring. After allowing the mixture to cool (under 0° C.), a solution of 4-(2-aminophenethyl)-2,6-di-tert-butylphenol (1.0 g, 3.1 mmol) in toluene (4 ml) was added dropwise. The solution was warmed up to room temperature and stirred overnight. After distilling off the solvent and purification of the residue by a silica gel column chromatography, recrystallization from ethyl acetate/hexane afforded N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(4-hexyloxyphenyl)urea (1.2 g, 71% yield). m.p. 174°-176° C.

出典