Diethylene glycol bis(3-aminopropyl) ether → 2-{1-[3-(2-{2-[3-(4-dicyanomethylene-2,6-dimethyl-4H-pyridin-1-yl)-propoxy]-ethoxy}-ethoxy)-propyl]-2,6-dimethyl-1H-pyridin-4-ylidene}-malononitrile
Reaction equation
[CH3:1][C:2]1O[C:4]([CH3:13])=[CH:5][C:6](=[C:8]([C:11]#[N:12])[C:9]#[N:10])[CH:7]=1.[CH2:14]([NH2:28])[CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][CH2:26][NH2:27]>>[C:9]([C:8]([C:11]#[N:12])=[C:6]1[CH:7]=[C:2]([CH3:1])[N:27]([CH2:26][CH2:25][CH2:24][O:23][CH2:22][CH2:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][CH2:14][N:28]2[C:4]([CH3:13])=[CH:5][C:6](=[C:8]([C:9]#[N:10])[C:11]#[N:12])[CH:7]=[C:2]2[CH3:1])[C:4]([CH3:13])=[CH:5]1)#[N:10]Participants
3
Procedure
A solution of 0.52 g (3 mmol) of (2,6-dimethyl-4H-pyran-4-ylidene)malononitril and 0.3 ml (1.5 mmol) of 4,7,10-trioxa-1,13-tridecanediamine in 6 ml of acetontrile was heated to 90° C. for 70 h under nitrogen. Removal of the acetonitrile left a brown residue which was recrystallized from 25 ml methanol and 10 ml ethyl acetate yielding 0.68 g (43%) of 2-{1-[3-(2-{2-[3-(4-dicyanomethylene-2,6-dimethyl-4H-pyridin-1-yl)-propoxy]-ethoxy}-ethoxy)-propyl]-2,6-dimethyl-1H-pyridin-4-ylidene}-malononitrile.
Workup
- customRemoval of the acetonitrile
- waitleft a brown residue which
- customwas recrystallized from 25 ml methanol and 10 ml ethyl acetate yielding 0.68 g (43%) of 2-{1-[3-(2-{2-[3-(4-dicyanomethylene-2,6-dimethyl-4H-pyridin-1-yl)-propoxy]-ethoxy}-ethoxy)-propyl]-2,6-dimethyl-1H-pyridin-4-ylidene}-malononitrile
Sources & evidence
- ORD record
- ord-185f83d30d51415380fa6dedfd0b8776
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07611696B2
Reaction notes
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