Reacción #5931

Ecuación de reacción

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

Rendimiento 65.1%

Disolventes

dimethylsulfoxide

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe mixture is extracted with ethyl acetate
2. 2
   LavadoThe ethyl acetate layer is washed
3. 3
   workup.DISTILLATIONdistilled
4. 4
   Otroto remove the solvent
5. 5
   OtroThe residue is purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=5:1)
6. 6
   Otrofurther is recrystallized from methanol

Procedimiento

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.

Fuente