Reaktion #82923

Reaktionsgleichung

[2,2-dichloro-1-[3-(trifluoromethyl)phenyl]ethylidene]hydrazinecarboxylic acid ethyl ester

Diisopropylethylamine

Ethyl propiolate

morpholine

→

6-(4-morpholinyl)-3-[3-(trifluoromethyl)phenyl]-1,5(6H)-pyridazindicarboxylic acid diethyl ester

Ausbeute 55.0%

Lösungsmittel

methylene chloride

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise over 15 min
2. 2
   TemperaturThe mixture was then refluxed for 30 min.
3. 3
   TemperaturThe mixture was then refluxed for 18 h
4. 4
   Temperaturcooled
5. 5
   Sonstigepartitioned 2 times with water
6. 6
   TrocknenThe organic layer was dried (MgSO4)
7. 7
   Filtrationfiltered
8. 8
   Sonstigeevaporated in vacuo
9. 9
   Sonstigeto give a crude solid
10. 10
    SonstigeThis solid was recrystallized from cyclohexane/ethyl acetate

Vorschrift

Ethyl propiolate (3.43 g, 0.035 mole) was stirred under N2 in methylene chloride (300 mL) at RT while morpholine (3.05 g, 0.035 mole) was added dropwise over 15 min. The mixture was then refluxed for 30 min. and then cooled to room temperature (RT). Diisopropylethylamine (5.65 g, 0.0437 mole) was then added to the mixture followed by the addition of [2,2-dichloro-1-[3-(trifluoromethyl)phenyl]ethylidene]hydrazinecarboxylic acid ethyl ester (10 g, 0.029 mole) which was added dropwise as a solution in methylene chloride (60 mL) over 30 min. The mixture was then refluxed for 18 h, cooled, and partitioned 2 times with water. The organic layer was dried (MgSO4), filtered and evaporated in vacuo to give a crude solid. This solid was recrystallized from cyclohexane/ethyl acetate to give 6-(4-morpholinyl)-3-[3-(trifluoromethyl)phenyl]-1,5(6H)-pyridazindicarboxylic acid diethyl ester (7.26 g, 55% yield) as a yellow solid, mp=128°-129° C.

Quelle