Reacción #556506

Ecuación de reacción

thionyl chloride

3,6-dichloro-pyridazine-4-carboxylic acid

aluminium trichloride

4-methyl-3H-benzoxazol-2-one

→

6-(3.6-dichloro-pyridazine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

Disolventes

1,2-dichloroethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was refluxed for 2 h
2. 2
   OtroThe reaction mixture was evaporated to dryness
3. 3
   workup.STIRRINGThen it was stirred for a further 2 h at 120° C., 3 h at 130° C.
4. 4
   Temperaturacooled for 48 h at RT
5. 5
   Extracciónextracted with DCM
6. 6
   Lavadowashed with water
7. 7
   Otrodried on sodium sulphate
8. 8
   Filtraciónfiltered
9. 9
   Otroevaporated down i
10. 10
    OtroThe residue was triturated with DIPE, suction
11. 11
    Filtraciónfiltered
12. 12
    Otrodried

Procedimiento

2.00 mL (27.4 mmol) thionyl chloride were added to 1.92 g (9.95 mmol) 3,6-dichloro-pyridazine-4-carboxylic acid in 10 mL 1,2-dichloroethane and the mixture was refluxed for 2 h. The reaction mixture was evaporated to dryness and coevaporated with 1,2-dichloroethane. Then 5.30 g (39.8 mmol) aluminium trichloride and 1.56 g (10.5 mmol) 4-methyl-3H-benzoxazol-2-one were added and the mixture was stirred for 1 h at 100° C. under a nitrogen atmosphere. Then it was stirred for a further 2 h at 120° C., 3 h at 130° C. and then cooled for 48 h at RT. The mixture was decomposed with ice water and extracted with DCM. The organic phases were combined, washed with water, dried on sodium sulphate, filtered and evaporated down i. vac. The residue was triturated with DIPE, suction filtered and dried.

Fuente