反应 #2286330

反应方程式

(2-cyano-2-{[3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-hydrazono}-acetyl)-carbamic acid ethyl ester

(2-Cyano-2-{[3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-hydrazono}-acetyl)-carbamic acid ethyl ester

potassium acetate

acetic acid

water

→

2-[3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo -1,6-dihydro-pyridazin-3-yloxy)-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro[1,2,4]triazine-6-carbonitrile

收率 85.8%

2-[3,5-Dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carbonitrile

收率 85.8%

溶剂

N,N-dimethylacetamide

acetonitrile

反应条件

后处理

1. 1
   其他The solids which resulted
2. 2
   过滤were collected by filtration
3. 3
   洗涤washed with water (65 mL)
4. 4
   其他dried under vacuum
5. 5
   其他to give an orange solid
6. 6
   温度heated
7. 7
   温度to reflux for 3 h
8. 8
   温度cooled to room temperature
9. 9
   过滤The resulting solids were then collected by filtration
10. 10
    洗涤washed with acetonitrile (12 mL) and methyl tert-butyl ether (24 mL)
11. 11
    其他dried under vacuum

实验过程

A solution of (2-cyano-2-{[3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-hydrazono}-acetyl)-carbamic acid ethyl ester (68) (6.5 g, 13.12 mmol) and potassium acetate (1.42 g, 14.43 mmol) in N,N-dimethylacetamide was heated to 120° C. for 2 h. At this time, the reaction was cooled to room temperature and was treated with glacial acetic acid (1.5 mL) and water (65 mL). The mixture was stirred at room temperature for 15 min. The solids which resulted were collected by filtration, washed with water (65 mL) and dried under vacuum to give an orange solid. The solid was suspended in acetonitrile (36 mL), heated to reflux for 3 h and then cooled to room temperature. The resulting solids were then collected by filtration, washed with acetonitrile (12 mL) and methyl tert-butyl ether (24 mL) and dried under vacuum to afford 2-[3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo -1,6-dihydro-pyridazin-3-yloxy)-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro[1,2,4]triazine-6-carbonitrile (69) (5.06 g, 85.8%) as an orange solid; ES(+)-HRMS m/e calcd for C18H14Cl2N6O4 (M+H)+ 449.0527, found 449.0527. Exact Mass=448.0454; Molecular Weight=449.26.

来源