반응 #5931

반응 방정식

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

수율 65.1%

용매

dimethylsulfoxide

반응 조건

후처리

1. 1
   추출the mixture is extracted with ethyl acetate
2. 2
   세척The ethyl acetate layer is washed
3. 3
   workup.DISTILLATIONdistilled
4. 4
   기타to remove the solvent
5. 5
   기타The residue is purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=5:1)
6. 6
   기타further is recrystallized from methanol

실험 절차

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.

출처