反応 #5931

反応方程式

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

収率 65.1%

溶媒

dimethylsulfoxide

反応条件

後処理

1. 1
   抽出the mixture is extracted with ethyl acetate
2. 2
   洗浄The ethyl acetate layer is washed
3. 3
   workup.DISTILLATIONdistilled
4. 4
   その他to remove the solvent
5. 5
   その他The residue is purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=5:1)
6. 6
   その他further is recrystallized from methanol

実験手順

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.

出典