反応 #2286330

反応方程式

(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

収率 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

収率 85.8%

溶媒

N,N-dimethylacetamide

acetonitrile

反応条件

後処理

1. 1
   その他The solids which resulted
2. 2
   ろ過were collected by filtration
3. 3
   洗浄washed with water (65 mL)
4. 4
   その他dried under vacuum
5. 5
   その他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
   ろ過The resulting solids were then collected by filtration
10. 10
    洗浄washed with acetonitrile (12 mL) and methyl tert-butyl ether (24 mL)
11. 11
    その他dried under vacuum

実験手順

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.

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