Reacción #322451

Ecuación de reacción

N-methylformanilide

2-(4 -chlorophenyl)-2,5,6,7-tetrahydro-3H-thieno-[2',3':6,7]cyclohepta[1,2-c]pyridazin-3-one

→

2-(4-chlorophenyl)-9-formyl-2,5,6,7-tetrahydro-3H-thieno-[2',3':6,7]-cyclohepta[1,2-c]pyridazin-3-one

Rendimiento 46.1%

Disolventes

oxychloride

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGAfter stirring at room temperature for 2 hours
2. 2
   workup.ADDITIONthe mixture was poured into ice-cold water
3. 3
   Extracciónextracted with ethyl acetate
4. 4
   LavadoThe extract was washed with water
5. 5
   Secadodried over anhydrous magnesium sulfate
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   OtroThe residue was chromatographed on a silica gel (SiO2 :40 g) column
8. 8
   OtroThe resulting solid was recrystallized from a mixed solvent of chloroform and ethanol

Procedimiento

A mixture of 0.45 g of N-methylformanilide in 0.33 ml of phosphrus oxychloride was stirred at room temperature for an hour and 0.5 g of 2-(4 -chlorophenyl)-2,5,6,7-tetrahydro-3H-thieno-[2',3':6,7]cyclohepta[1,2-c]pyridazin-3-one was added thereto. After stirring at room temperature for 2 hours, the mixture was poured into ice-cold water and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was chromatographed on a silica gel (SiO2 :40 g) column using chloroform as an eluent. The resulting solid was recrystallized from a mixed solvent of chloroform and ethanol to give 0.25 g of 2-(4-chlorophenyl)-9-formyl-2,5,6,7-tetrahydro-3H-thieno-[2',3':6,7]-cyclohepta[1,2-c]pyridazin-3-one as a pale yellow powder, melting at 170°-172° C.

Fuente