2-(Ethoxymethylene)propanedinitrile → HCID 18689500, compound
Reaction equation
[Cl:1][C:2]1[C:3]([NH:13][NH2:14])=[N:4][C:5]([Cl:12])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C(O[CH:18]=[C:19]([C:22]#[N:23])[C:20]#[N:21])C>C(O)C>[NH2:23][C:22]1[N:13]([C:3]2[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:10])([F:11])[F:9])=[C:5]([Cl:12])[N:4]=2)[N:14]=[CH:18][C:19]=1[C:20]#[N:21]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
24.6 g (0.1 mol) of 3,6-dichloro-2-hydrazino-5-trifluoromethylpyridine were added to a mixture of 12.2 g (0.1 mol) of ethoxymethylenemalononitrile and 200 ml of ethanol with stirring at 20° C. and it was stirred at 78° C. for 10 hours. After cooling, the reaction mixture was concentrated under reduced pressure and the residue was taken up in methylene chloride. It was extracted 3× with water and the organic phase separated off was dried over magnesium sulfate, filtered off with suction through neutral alumina and then concentrated under reduced pressure. After stirring in ether/pentane, 13.3 g (41.3% of theory) of the title compound of m.p. 168-171° C. were obtained (Active Compound Example No. 2a.002).
Workup
- stirringit was stirred at 78° C. for 10 hours
- temperatureAfter cooling
- concentrationthe reaction mixture was concentrated under reduced pressure
- extractionIt was extracted 3× with water
- customthe organic phase separated off
- dry with materialwas dried over magnesium sulfate
- filtrationfiltered off with suction through neutral alumina
- concentrationconcentrated under reduced pressure
- stirringAfter stirring in ether/pentane
Sources & evidence
- ORD record
- ord-814137766be24e4eba8160aa1dd879d8
- Source dataset
- uspto-grants-2000_08
- Patent number
- US06107253
Reaction notes
Loading…