ethyl 2,2-dichlorocyanoacetate

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Properties of substance:

ethyl 2,2-dichlorocyanoacetate

Synonyms:

ethyl 2,2-dichloro-2-cyanoacetate

Group of substances:

organic

Empirical formula (Hill's system for organic substances):

C₅H₅Cl₂NO₂

Structural formula as text:

NCCCl2COOC2H5

Molar/atomic mass: 182.0047

Synthesis 1:

Reference: McBee, E. T., Higgins, J. F., Pierce, O. R. The Synthesis of Ethyl 2,2-Dichlorocyanoacetate / Journal of the American Chemical Society. - 1951. - Vol. 73, No. 11 pp. 5473 [doi: 10.1021/ja01155a539]

NCCH₂COOC₂H₅ + 2Cl₂ → NCCCl₂COOC₂H₅ + 2HCl

Ethyl cyanoacetate (226 g., 2.0 moles) was placed in a glass chlorination tube 90 cm. long and 20 cm. in diameter. Chlorine was introduced through a gas diffusion disc beneath the surface of the ester. A condenser was attached to the top of the chlorination tube. An attached water scrubber was used to remove hydrogen chloride and excess chlorine. The tube was maintained at 140° while the chlorine was introduced. Chlorine was admitted until no more was absorbed. The reaction product was then warmed on a steam-bath for two hours to remove dissolved gases and rectified under reduced pressure. A 90% yield of ethyl 2,2-dichlorocyanoacetate was obtained, b.p. 60° at 19 mm., n(20 С,D) 1.4380, d(20/4) 1.238.

Anal. Calcd. for C5H5Cl2NO2: C, 33.2; H, 2.74. Found: C, 32.9; H, 2.74.

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