반응 #5924

반응 방정식

methyl α-bromo-4-chlorophenylacetate

1-amino-2-naphthalenethiol

sodium borohydride

sodium acetate

→

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

수율 86.0%

용매

ethanol

acetic acid

반응 조건

후처리

1. 1
   workup.WAITthe mixture is sitrred at room temperature under argon overnight
2. 2
   기타the resulting precipitate is separated by filtration
3. 3
   세척washed
4. 4
   기타dried
5. 5
   기타recrystallized from tetrahydrofuran-n-hexane

실험 절차

To a solution of 1-amino-2-naphthalenethiol (27.81 g) in ethanol (500 ml) is added sodium borohydride (11.35 g) at room temperature. The mixture is stirred for 20 minutes, and thereto is added dropwise acetic acid (200 ml) and is further added sodium acetate (24.6 g). To the mixture is further added dropwise methyl α-bromo-4-chlorophenylacetate (46.8 g), and the mixture is sitrred at room temperature under argon overnight. The reaction mixture is poured into ice water and the resulting precipitate is separated by filtration, washed, dried and recrystallized from tetrahydrofuran-n-hexane to give 3-(4-chlorophenyl)-1H-naphtho-[2,1-b][1,4]thiazin-2(3H)-one (44.45 g, yield 82.6%) as crystals.

출처