반응 #5330

반응 방정식

hydroxylamine hydrochloride

triethylamine

tetrahydrofuran

compound

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

→

title compound

수율 76.0%

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

수율 76.0%

용매

DMSO

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture was stirred for 60 hours at 70° C
2. 2
   기타After removal of crystalline precipitate
3. 3
   여과by filtration
4. 4
   농축the filtrate was concentrated to dryness
5. 5
   기타The residue was partitioned between water (1.2 liter) and ethyl acetate (350 ml)
6. 6
   세척the upper layer was washed with water (70 ml×3)
7. 7
   기타Ethyl acetate was evaporated under reduced pressure
8. 8
   workup.ADDITIONto the residue was added methanol (70 ml)
9. 9
   여과Resulting crystalline precipitate was filtered off
10. 10
    농축The filtrate was concentrated to dryness under reduced pressure

실험 절차

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%).

출처