Reacción #5928

Ecuación de reacción

acryloyl chloride

3-(4-chlorophenyl)-2,3-dihydro1H-naphtho[2,1-b][1,4]thiazine

sodium hydrogen carbonate

water

→

3-(4-chlorophenyl)-1-propenoyl-2,3-dihydro-1H-naphtho[2,1-b][1,4]thiazine

Rendimiento 78.0%

Disolventes

methylene chloride

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONis added dropwise
2. 2
   OtroThe organic layer is separated
3. 3
   Lavadowashed
4. 4
   Otrodried
5. 5
   workup.DISTILLATIONdistilled
6. 6
   Otroto remove the solvent
7. 7
   OtroThe residue is chromatographed on silica gel (toluene : acetone =50 : 1)

Procedimiento

To a mixture of 3-(4-chlorophenyl)-2,3-dihydro1H-naphtho[2,1-b][1,4]thiazine (1.50 g), sodium hydrogen carbonate (1.0 g), methylene chloride (30 ml) and water (15 ml) is added dropwise with stirring a solution of acryloyl chloride (0.90 g) in methylene chloride (10 ml) under ice cooling. The mixture is stirred at room temperature for 3 hours. The organic layer is separated, washed, dried and distilled to remove the solvent. The residue is chromatographed on silica gel (toluene : acetone =50 : 1) to give 3-(4-chlorophenyl)-1-propenoyl-2,3-dihydro-1H-naphtho[2,1-b][1,4]thiazine (1.37 g, 78 %) as powder.

Fuente