تفاعل #5931

معادلة التفاعل

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

المردود 65.1%

المذيبات

dimethylsulfoxide

ظروف التفاعل

المعالجة

1. 1
   استخلاصthe mixture is extracted with ethyl acetate
2. 2
   غسيلThe ethyl acetate layer is washed
3. 3
   workup.DISTILLATIONdistilled
4. 4
   أخرىto remove the solvent
5. 5
   أخرىThe residue is purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=5:1)
6. 6
   أخرىfurther is recrystallized from methanol

الإجراء التجريبي

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.

المصدر