2-Cyano-N-phenylacetamide

yellowish crystalline powder

Toa mixture of ester and amine in a 20 mL round bottomed flask was added [PyPS]Cyanoacetic acid (0.96 g, 11.1 mmol, 1 eq) was added to a mixture of PC1Cyanoacetic acid (1. 0 g, 11. 7 mmol) is added to a stirred suspension of PCl5 (2. 4 g, 11. 7 mmol) in dry dichloromethane (200 ml). The reaction mixture is heated to reflux and kept stirring for 30 min. After cooling to rt, aniline (1. 07 ml, 11. 7 mmol) is added dropwise and the reaction is stirred at reflux for additional 2 h, then cooled to 0°C and neutralized by addition of aqueous saturated Na2C03 solution. The precipitate is filtered off, washed with water and dried under high vacuum to give title compound (1. 54 g) as a white solid in 82percent yield : tR (LC-2) 1. 50 min, ESI-MS (+) : m/z 183. 33 [M+Na] + (calcd 160. 17 for C9H8N2O).General procedure: To the well-stirred solution of aniline (11.78 mL, 129.3 mmol) and cyanoacetic acid (10 g, 117.5 mmol) in dry tetrahydrofuran (90 mL) was added N, N'-diisopropyl carbodimide (18.3 mL, 117.5 mmol) drop-wise over 15 min and the reaction mixture was further stirred at room temperature for 5 h. The precipitated urea derivative was removed by filtration and the filtrate containing the product was evaporated to give the crude product. The crude product was crystallized from ethanol to yield 11.9 g of the product as a white crystalline solid.

Molecular Weight:160.17
XLogP3:1.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:160.063662883
Monoisotopic Mass:160.063662883
Topological Polar Surface Area:52.9
Heavy Atom Count:12
Complexity:198
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes