Reacción #5330

Ecuación de reacción

hydroxylamine hydrochloride

triethylamine

tetrahydrofuran

compound

Methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]2-propylthiobenzimidazole-7-carboxylate

→

title compound

Rendimiento 76.0%

Methyl 1-[(2'-(hydroxycarbamimidoyl)biphenyl-4-yl)methyl]-2-propylthiobenzimidazole-7-carboxylate

Rendimiento 76.0%

Disolventes

DMSO

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture was stirred for 60 hours at 70° C
2. 2
   OtroAfter removal of crystalline precipitate
3. 3
   Filtraciónby filtration
4. 4
   Concentraciónthe filtrate was concentrated to dryness
5. 5
   OtroThe residue was partitioned between water (1.2 liter) and ethyl acetate (350 ml)
6. 6
   Lavadothe upper layer was washed with water (70 ml×3)
7. 7
   OtroEthyl acetate was evaporated under reduced pressure
8. 8
   workup.ADDITIONto the residue was added methanol (70 ml)
9. 9
   FiltraciónResulting crystalline precipitate was filtered off
10. 10
    ConcentraciónThe filtrate was concentrated to dryness under reduced pressure

Procedimiento

To a solution of hydroxylamine hydrochloride (20.85 g) in DMSO (200 ml) was added triethylamine (3.9 g) and the mixture was stirred for 30 minutes at room temperatures. To the reaction mixture was added the compound (16 g) obtained in Example (34c), and the mixture was stirred for 60 hours at 70° C. To the resultant mixture was added tetrahydrofuran (100 ml). After removal of crystalline precipitate by filtration, the filtrate was concentrated to dryness. The residue was partitioned between water (1.2 liter) and ethyl acetate (350 ml), and the upper layer was washed with water (70 ml×3). Ethyl acetate was evaporated under reduced pressure, and to the residue was added methanol (70 ml). Resulting crystalline precipitate was filtered off. The filtrate was concentrated to dryness under reduced pressure to give the title compound as a pale yellow syrup (13.0 g, 76%).

Fuente