Реакция #429855

Уравнение реакции

diphenylphosphinic chloride

4-geranyloxybenzoic acid

2-(2-aminoethylthio)-5-methoxypyridine

→

aimed compound

Выход 92.1%

2-[2-(4-geranyloxybenzoylamino)ethylthio]-5-methoxypyridine

Выход 92.1%

Растворители

triethylamine

chloroform

Условия реакции

Обработка

1. 1
   Температураwhile being cooled with ice
2. 2
   workup.STIRRINGwas stirred for 17 hours at room temperature
3. 3
   ПромывкаThe reaction mixture was washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively
4. 4
   Сушкаdried over sodium sulfate anhydride
5. 5
   Концентрированиеconcentrated under a vacuum
6. 6
   ДругоеThe residue was purified by silica gel column chromatography (chloroform:methanol=20:1)
7. 7
   ДругоеThe resulting solid was recrystallized from n-hexane/ethyl acetate

Методика

4-geranyloxybenzoic acid(1.92 g) was dissolved in chloroform(40 ml) and triethylamine(1.95 ml), and then diphenylphosphinic chloride(1.34 ml) was added thereto while being cooled with ice. After being stirred for 1 hour, the mixture, with 2-(2-aminoethylthio)-5-methoxypyridine(1.29 g) added thereto, was stirred for 17 hours at room temperature. The reaction mixture was washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and then concentrated under a vacuum. The residue was purified by silica gel column chromatography (chloroform:methanol=20:1). The resulting solid was recrystallized from n-hexane/ethyl acetate, thereby yielding 2.84 g of the aimed compound.

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