Triethylamine → HCID 131731791, compound

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Reaction Steps

To a mixture of 4-cyanophenylhydrazine HCl (3.44 g, 20.3 mM) and 6-chlorohexanal (2.5 g, 18.6 mM) in toluene (30 mL) was added triethylamine at 0° C. (2.82 mL, 20.3 mM). The mixture was allowed to stir for 2 hours at ambient temperature. The mixture was filtered and the resultant filter cake was washed with toluene. The combined filtrate was concentrated under vacuum to give 4.92 g of a crude product, which was purified using conventional methods to yield 4.16 g (89.6%) of 4-(2-(6-chlorohexylidene)hydrazinyl)benzonitrile as a mixture of cis:trans isomers (ratio 5:1). NMR (400 MHZ, CDCl3): 7.6-6.6 (6H, (4H, dd-aromatic; 1H (m)-NH, 1H (t)-N═CH-t)), 3.57 (2H (t), CH2Cl), 2.2-2.4 (2H (m), ═CH—CH2), 1.75-1.90 (2H (m), CH2Cl—CH2), 1.49-1.65 (4H (m), CH2—CH2); m/z: 250 [M+H]+, calcd for [C13H16ClN3+H]+ 250.10.

Provenance & Evidence