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ChemicalBook CAS DataBase List 2-[3-(DIMETHYLAMINO)-1-METHOXY-2-PROPENYLIDENE]MALONONITRILE
95689-38-6

2-[3-(DIMETHYLAMINO)-1-METHOXY-2-PROPENYLIDENE]MALONONITRILE synthesis

5synthesis methods
4637-24-5 Synthesis
N,N-Dimethylformamide dimethyl acetal

4637-24-5
633 suppliers
$5.00/25g

5417-82-3 Synthesis
(1-ETHOXYETHYLIDENE)MALONONITRILE

5417-82-3
123 suppliers
$9.00/1g

Propanedinitrile, 2-[3-(dimethylamino)-1-ethoxy-2-propen-1-ylidene]-

98645-41-1
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inquiry

-

Yield:-

Reaction Conditions:

at 100; for 1 h;

Steps:

41.41A
Example 41 A; 2-(3-dimethylamino-l-ethoxyallylidene)malononitrile:; 2-(l-ethoxyethylidene)malono-nitrile (110.0 g, 808 mmol) was dissolved in TV, /V- dimethylformamide dimethyl acetal (94%, 230 mL, 1.62 mol), and the reaction mixture was heated to reflux at 100 0C for 1 hr. Cooled down to room temperature. Solid was collected, and washed with cold methanol to give an orange solid product. The mother liquor was concentrated, and the solid was collected again, and washed with cold methanol. This procedure was repeated couple of times, and all the solid products were combined. The final residue was purified by a short column chromatography (SiO2, ethyl acetate). The combined yield of the reaction is 78% (120.0 g) as a mixture of 2-(3-dimethylamino-l-ethoxy- allylidene)malononitrile (73.5%) and 2-(3-dimethylamino-l-methoxyallylidene)malono- nitrile (26.5%). EPO 2-(3-dimethylamino-l-ethoxyallylidene)malononitrile: 1H NMR (CDCl3, 300 MHz): δ = 7.47 ppm (d, J= 12.6 Hz, IH); 5.16 (d, J= 12.6 Hz, IH); 4.43 (q, J= 7.1 Hz, 2H), 3.19 (s, br. 3H), 2.94 (s, br. 3H), 1.41 (t, J= 7.1 Hz, 3H). MS (ESI, M+l): 192.1. 2-(3-dimethylamino-l-metlioxyallylidene)malononitrile: 1H NMR (CDCl3, 300 MHz): δ = 7.51 ppm (d, J= 12.9 Hz, IH); 5.10 (d, J= 12.9 Hz, IH); 4.11 (s, 3H), 3.19 (s, br. 3H), 2.94 (s, br. 3H). MS (ESI, M+l): 178.0.

References:

ABBOTT LABORATORIES WO2006/81072, 2006, A1 Location in patent:Page/Page column 47-48

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