Reacción #9265

Ecuación de reacción

[2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-6-nitro-1,3-benzothiazol-7-yl]methyl cyanide

triethylamine

trimethylsilyl chloride

→

2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl) [1,3]thiazolo[5′,4′: 3,4]benzo[c]isoxazol-8-yl cyanide

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was quenched
2. 2
   workup.ADDITIONby pouring into dilute aqueous hydrochloric acid
3. 3
   Extracciónthen extracted well with ethyl acetate
4. 4
   ExtracciónThe combined organics were back extracted with dilute sodium bicarbonate
5. 5
   Secadothen dried over magnesium sulfate
6. 6
   Concentraciónconcentrated
7. 7
   OtroThe dark oil was further purified by preparative HPLC

Procedimiento

0.2 g of [2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-6-nitro-1,3-benzothiazol-7-yl]methyl cyanide was charged into about 2 ml dimethylformamide. About 15 equivalents of triethylamine were then added followed by about 15 equivalents of trimethylsilyl chloride. The solution was stirred at room temperature for about 4–20 hours. The reaction was quenched by pouring into dilute aqueous hydrochloric acid then extracted well with ethyl acetate. The combined organics were back extracted with dilute sodium bicarbonate then dried over magnesium sulfate and concentrated. The dark oil was further purified by preparative HPLC to yield 2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl) [1,3]thiazolo[5′,4′: 3,4]benzo[c]isoxazol-8-yl cyanide.

Fuente