반응 #1957952

반응 방정식

diethylether

6-[N-(2-Benzyloxy-5-bromobenzyl)-N-ethylamino]pyridazine-3-carboxamide

boron trichloride dimethyl sulphide

sodium bicarbonate

→

6-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]-pyridazine-3-carboxamide

수율 52.3%

용매

methanol

Dichloromethane

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   기타to give a pH of around 9
2. 2
   기타the organic and aqueous layers separated
3. 3
   세척the aqueous layer washed with dichloromethane
4. 4
   세척The combined organic extracts were then washed with brine
5. 5
   기타dried
6. 6
   기타evaporated
7. 7
   기타to give a sticky solid
8. 8
   workup.WAITleft at ambient temperature overnight
9. 9
   여과The resultant solid was filtered
10. 10
    세척washed with diethylether
11. 11
    기타sucked dry

실험 절차

6-[N-(2-Benzyloxy-5-bromobenzyl)-N-ethylamino]pyridazine-3-carboxamide (3.24 g, 7.3 mmol) in dichloromethane (50 ml) was treated with boron trichloride dimethyl sulphide reagent (18.5 ml, 2M solution) in dichloromethane (37 mmol) and the solution stirred at ambient temperature for 6 days. The mixture was carefully treated with excess aqueous sodium bicarbonate solution to give a pH of around 9. Dichloromethane was added, the organic and aqueous layers separated and the aqueous layer washed with dichloromethane. The combined organic extracts were then washed with brine, dried and evaporated to give a sticky solid. This was treated with diethylether (30 ml) and methanol (3 ml) and left at ambient temperature overnight. The resultant solid was filtered, washed with diethylether and sucked dry to give 6-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]-pyridazine-3-carboxamide (1.34 g, 52%).

출처