Реакция #5931

Уравнение реакции

water

3-(4-chlorophenyl)-1H-naphtho-[2,1-b][1,4]thiazin-2(3H)-one

sodium hydroxide

1-bromo-3-chloropropane

→

3-(4-chlorophenyl)-1-(3-chloropropyl)-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-one

Выход 65.1%

Растворители

dimethylsulfoxide

Условия реакции

Обработка

1. 1
   Экстракцияthe mixture is extracted with ethyl acetate
2. 2
   ПромывкаThe ethyl acetate layer is washed
3. 3
   workup.DISTILLATIONdistilled
4. 4
   Другоеto remove the solvent
5. 5
   ДругоеThe residue is purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=5:1)
6. 6
   Другоеfurther is recrystallized from methanol

Методика

To a solution of 3-(4-chlorophenyl)-1H-naphtho-[2,1-b][1,4]thiazin-2(3H)-one (10.0 g) and 96% sodium hydroxide (1.96 g) in dimethylsulfoxide (150 ml) is added 1-bromo-3-chloropropane (6.78 g) under ice cooling, and the mixture is stirred at room temperature overnight. The reaction mixture is poured into water, and the mixture is extracted with ethyl acetate. The ethyl acetate layer is washed and distilled to remove the solvent. The residue is purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=5:1) and further is recrystallized from methanol to give 3-(4-chlorophenyl)-1-(3-chloropropyl)-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-one (8.04 g). M.p. 110°-112.5° C.

Источник