Reacción #833556

Ecuación de reacción

3,4-dihydro-2-methyl-3-oxo-2H-naphtho[2,3-e]-1,2-thiazine 1,1-dioxide

triethylamin

phenylisocyanate

→

3,4-dihydro-2-methyl-3-oxo-2H-naphtho[2,3-e]-1,2-thiazine-4-carboxanilide 1,1-dioxide

Rendimiento 37.0%

Disolventes

DMSO

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas quenched with dilute HCl in an ice bath
2. 2
   Extracciónextracted with ether (2 times)
3. 3
   LavadoThe combined ether extracts were washed
4. 4
   Otrodried
5. 5
   Concentraciónconcentrated
6. 6
   Otroto give 1.9 g crude product
7. 7
   OtroThis material was recrystallized from ethanol
8. 8
   Otrofollowed by recrystallization from ethylacetate

Procedimiento

To a solution of 1.3 g (5 mmol) 3,4-dihydro-2-methyl-3-oxo-2H-naphtho[2,3-e]-1,2-thiazine 1,1-dioxide and 0.7 ml (5 mmol) triethylamin dissolved in 10 ml DMSO at room temperature was added 0.6 g (5 mmol) phenylisocyanate. After stirring for 20 hr the resulting mixture was quenched with dilute HCl in an ice bath and then extracted with ether (2 times). The combined ether extracts were washed, dried and concentrated to give 1.9 g crude product. This material was recrystallized from ethanol followed by recrystallization from ethylacetate to give 0.7 g 3,4-dihydro-2-methyl-3-oxo-2H-naphtho[2,3-e]-1,2-thiazine-4-carboxanilide 1,1-dioxide.

Fuente