Cyclohexylidenemalononitrile

The corresponding reactions (a) to (p) have been achieved through reactions, under agitation and in 5 ml of solvent (dimethylformamide(ine?) DMF or acetonitril MeCN), of 1 millimole of carbonyl compound and 1 millimole of activated methanol, in the presence of 0.0035 g of 'HDT-F' catalyst prepared in example 1. In each case, the progress of the reaction was followed by chromatography on a plate. At the end of the reaction the catalyst was filtered, the filtrate was washed with water and the product was extracted by sodium sulphate and concentrated under low pressure. The indicated yield was calculated on the basis of NMR spectra observed at the final medium, on the basis of R1R2CO ketonic compounds quantity consumed during the reaction.General procedure: A mixture of carbonyl compound (0.5 mmol), activated methylene compound (0.5 mmol), IL catalyst (10 mol percent) and water (1 mL) was stirred at room temperature in 25-mL round bottomed flask. Upon completion of the reaction (monitored by TLC), the reaction mixture always solidified in the round bottomed flask. Then the solidified mixture was filtered and washed with cold water (5 mL) to remove the IL catalyst, and evaporated under reduced pressure to obtain the target products. The products of 3o, 3p, 3q, 3x, 3c’, 3d’ are colourless oil, and they were purified by column chromatography on silica gel using petroleum ether/ethyl acetate as the eluent after the solvent was removed under reduced pressure. The products of 3j’, 3k’were prepared under solvent-free condition; After completion of the reaction, the solidified mixture was washed with ethanol (5 mL) to remove the IL catalyst, and evaporated under reduced pressure to obtain the target products.General procedure: A mixture of activated methylene compound 4 (0.5 mmol), carbonyl compound 5 (0.5 mmol), IL catalyst (10 mol percent) and water (1 mL) was stirred at room temperature in a 25 mL round bottomed flask. Upon completion of the reaction (monitored by TLC), the reaction mixture always solidified in the round bottomed flask. Then the solidified mixture was filtered and washed with cold water (5 mL) to remove the IL catalyst, and evaporated under reduced pressure to obtain the target products 6. The produce of 6l were purified by column chromatography on silica gel using petroleum ether/ethyl acetate (8:1) as the eluent and got pure product after the solvent was removed under reduced pressure.General procedure: A mixture of 1a (232 mg, 2.0 mmol) and 2a (132 mg, 2.0 mmol) in H2O (0.5 mL) and DABCO (224 mg, 2.0mmol) was stirred at room temperature for 3 min until TLC showed complete disappearance of the starting materials. The mixture was extracted by EtOAc (5 mL) and the organic layer was washed with saturated solution of NaHCO3 and brine. The organic layer was dried over Na2SO4 . Product 3aa was obtained by evaporation of the volatile portion of the organic layer and was puried by recrystallization from EtOAc/hexane mixture. Product 3aa was obtained in 80percent yield (262 mg). The product was identied based on its physical and spectral characteristics. The remaining compounds 3ab-3db were synthesized in a similar manner.General procedure: A mixture of the aldehyde/ketone (0.1 mmol), compound of active methylene group (0.1 mmol), catalyst (5 mg)and solvent (toluene or water, 0.4 mL) was added in a glass tube and mechanically stirred at 75 °C. The reaction progress was monitored by Gas Cromatography with FID detector. After the completion of this reaction, the catalyst was removed by magnetic separation. For there actions in toluene, the mixture was purified by using column chromatography, and for the reactions in water, the product was precipitated with cool water, filtrated and dried under low pressure. All the products were characterized by A mixture of 1 mmol of cyclohexanone, 1 mmol of malonic acid dinitrile, and 0.08 mol percent of triethylamine in ethyl alcohol was refluxed for 30 min. The crystals were filtered off, washed with cold ethanol, and dried in air. Yield 0.40 g (60percent), mp 172–174°C (mp 173.5–174.5°C[6]). Found, percent: C 72.99; H 6.93; N 19.79. C9H10N2. Calculated: C 73.79; H 6.85; N 19.27.

Molecular Weight:146.19
XLogP3:1.9
Hydrogen Bond Acceptor Count:2
Exact Mass:146.084398327
Monoisotopic Mass:146.084398327
Topological Polar Surface Area:47.6
Heavy Atom Count:11
Complexity:242
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes