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

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

5synthesis methods

Product Name:2-[3-(DIMETHYLAMINO)-1-METHOXY-2-PROPENYLIDENE]MALONONITRILE
CAS Number:95689-38-6
Molecular formula:C9H11N3O
Molecular Weight:177.2

4637-24-5 Synthesis

4637-24-5
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5417-82-3 Synthesis

5417-82-3
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2-[3-(DIMETHYLAMINO)-1-METHOXY-2-PROPENYLIDENE]MALONONITRILE

95689-38-6
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Propanedinitrile, 2-[3-(dimethylamino)-1-ethoxy-2-propen-1-ylidene]-

98645-41-1
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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

4637-24-5 Synthesis

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

5417-82-3 Synthesis

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

95689-38-6
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inquiry

References