Реакция #5330

Уравнение реакции

hydroxylamine hydrochloride

triethylamine

tetrahydrofuran

compound

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

→

title compound

Выход 76.0%

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

Выход 76.0%

Растворители

DMSO

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe mixture was stirred for 60 hours at 70° C
2. 2
   ДругоеAfter removal of crystalline precipitate
3. 3
   Фильтрацияby filtration
4. 4
   Концентрированиеthe filtrate was concentrated to dryness
5. 5
   ДругоеThe residue was partitioned between water (1.2 liter) and ethyl acetate (350 ml)
6. 6
   Промывкаthe upper layer was washed with water (70 ml×3)
7. 7
   ДругоеEthyl acetate was evaporated under reduced pressure
8. 8
   workup.ADDITIONto the residue was added methanol (70 ml)
9. 9
   ФильтрацияResulting crystalline precipitate was filtered off
10. 10
    КонцентрированиеThe filtrate was concentrated to dryness under reduced pressure

Методика

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%).

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