反応 #5330

反応方程式

hydroxylamine hydrochloride

triethylamine

tetrahydrofuran

compound

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

→

title compound

収率 76.0%

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

収率 76.0%

溶媒

DMSO

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture was stirred for 60 hours at 70° C
2. 2
   その他After removal of crystalline precipitate
3. 3
   ろ過by filtration
4. 4
   濃縮the filtrate was concentrated to dryness
5. 5
   その他The residue was partitioned between water (1.2 liter) and ethyl acetate (350 ml)
6. 6
   洗浄the upper layer was washed with water (70 ml×3)
7. 7
   その他Ethyl acetate was evaporated under reduced pressure
8. 8
   workup.ADDITIONto the residue was added methanol (70 ml)
9. 9
   ろ過Resulting crystalline precipitate was filtered off
10. 10
    濃縮The filtrate was concentrated to dryness under reduced pressure

実験手順

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%).

出典