تفاعل #5924

معادلة التفاعل

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

المردود 86.0%

المذيبات

ethanol

acetic acid

ظروف التفاعل

المعالجة

1. 1
   workup.WAITthe mixture is sitrred at room temperature under argon overnight
2. 2
   أخرىthe resulting precipitate is separated by filtration
3. 3
   غسيلwashed
4. 4
   أخرىdried
5. 5
   أخرىrecrystallized from tetrahydrofuran-n-hexane

الإجراء التجريبي

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.

المصدر