(Z)-3-dimethylamino-2-isocyano-acrylic acid ethyl ester synthesis
- Product Name:(Z)-3-dimethylamino-2-isocyano-acrylic acid ethyl ester
- CAS Number:72130-97-3
- Molecular formula:C8H12N2O2
- Molecular Weight:168.2
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Yield: 75%
Reaction Conditions:
in ethanol at 0 - 25;
Steps:
(Z)-3-Dimethylamino-2-isocyano-acrylic acid ethyl ester
To a solution of ethyl-2-isocyanate (575 g, 5083 mmol) in EtOH (6.5 L) at 0°C was added dropwise 1,1-diethoxy-N,N-dimethanamine (1.2 L, 6608 mmol). The mixture was stirred at rt for 30 h. The reaction mixture was diluted with TBME (1.5 L), fixed on silica gel and filtered. The mother liquor was concentrated. The residue was purified by MPLC (Column 880 x 150 mm, 7 kg silica gel, Flow 1000 mL/min, heptane/EtOAc, 85:15 → 0:100). tR: 0.74 min (LC-MS 2); ESI-MS: 169.1 [M+H]+ (LC-MS 2); 1H-NMR (CDCl3, 400 MHz) δ (ppm) 7.15 (s, 2H), 4.18 (q, 2H), 3.20 (bs, 6H), 1.26 (t, 3H).
References:
Vaupel, Andrea;Holzer, Philipp;Ferretti, Stephane;Guagnano, Vito;Kallen, Joerg;Mah, Robert;Masuya, Keiichi;Ruetz, Stephan;Rynn, Caroline;Schlapbach, Achim;Stachyra, Thérèse;Stutz, Stefan;Todorov, Milen;Jeay, Sébastien;Furet, Pascal [Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,# 20,p. 3404 - 3408] Location in patent:supporting information
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5815-08-7
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2999-46-4
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