Research Journal of Chemical Sciences ______________________________________________ISSN 2231-606XVol. 4(5), 56-58, May (2014) Res.J. Chem. Sci. International Science Congress Association 56 SiOSupported Synthesis of N, N Disubstituted CinnamamidesRahimkhan U. Pathan and Santosh V. Agarkar Research laboratory of Chemistry, AEC, Chikhli, Dist-Buldana, 443201, M.S., INDIA Available online at: www.isca.in, www.isca.me Received 12thMarch2014, revised3thApril 2014, accepted 11thMay 2014Abstract In the present work SiO was use as solid support for reactants, which increases the rate of reaction and also support the easy separation of target product from phosphine oxide. Witting reagent (Phosphorous ylide) and aromatic aldehydes supported on SiO2 were treated under microwave irradiations to obtained respective N, N disubstituted Cinnamamide. This synthetic route was found to be convenient and energy efficient. Keywords: N, N disubstituted CINNAMAMIDES, SiO support. IntroductionNow a day’s N, N disubstituted Cinnamamides have been received much more attention due to their use in medicinal field1,2,3. Cinnamamides may be used as an intermediate or precursor in many organic syntheses and pharmaceutical formulations4,5. Literature survey exposes the value of cinnamamides and their applications in different fields6,7,8. Literature survey shows that several reactions were carried out by using solid support like silica and alumina and thousands of compounds were synthesized successfully by this method9,10. But the synthesis of cinnamamides by using solid support remains untouched. This literature survey encourage the author to undertake the present research work in which series of N, N disubstituted cinnamamides were synthesized under microwave irradiation by using SiO2 as a solid support11, 12. This synthetic approach was found to be convenient and energy efficient since it minimizes the use of solvent and prolong heating to the reaction mixture. Material and Methods All the required Chemicals were procured from Sigma Aldrich and S D Fine limited, Mumbai, and used without further purification. Microwave oven used is of LG make, model-MC3283AMPG. The progress of reactions was monitored by Thin Layer Chromatography (TLC plate method). And after completion of reactions, compounds were purified by column chromatography using silica (Mesh-160). Representative compounds were characterized by I.R., H NMR, 13C NMR and Mass spectroscopic techniques.. Melting Points of compounds were determined by open capillaries method on electro-thermal apparatus. General Method: SiO (160 mesh,5.0 g) was added to the solution of appropriate aldehyde (2a-k,2 mmol) and Witting reagent (1, 2.86 g, 2.6mmol) in dichloromethane (DCM) (10 ml) and reaction mixture was stirred for 2-5 minutes. The solvent was evaporated and remaining powder was air dried and spread in a Petri plate. The content was irradiated in a microwave oven till the completion of reaction (1-3 minutes). The Progress of reaction was monitored by thin layer chromatography (TLC). After completion of reaction, the products (3a-k) were separated by column chromatography by using silica mesh-160. Scheme-1 N, N disubstituted Cinnamamides R &R’= -CH, -CResults and Discussion N,N disubstituted Cinnamamides (3a-k) were prepared by simple and convenient SiO supported reaction pathway and the representative compounds were characterized by suitable techniques and the results were discussed as fallows. Research Journal of Chemical Sciences ___________________________________________________________ISSN 2231-606XVol. 4(5), 56-58, May (2014) Res. J. Chem. Sci. International Science Congress Association 57 Table-1 Various substituent’s of the compounds Entries R R R R RMolecular Formula 3a H H H H H C 11 H 13 NO 3b H H -OCH 3 H H C 12 H 15 N O 2 3c H -OCH 3 -OCH 3 H H C 13 H 17 N O 3 3d H -OCH 3 -OCH 3 -OCH 3 H C 14 H 19 N O 4 3e H -OCH 2 -O- H H C 12 H 13 N O 3 3f -NO 2 H H H H C 11 H 12 N 2 O 3 3g H H -Cl H H C 11 H 12 Cl NO 3h H H -NO 2 H H C 11 H 12 N 2 O 3 3i H H -N (CH 3 ) 2 H H C 13 H 18 N 2 O 3j H H -OH H H C 11 H 13 N O 2 3k H H H H H C 13 H 17 NO Table-2 List of N, N disubstituted Cinnamamides Prepared Entries Compound Yield (%) M.P. ( o C) 3a (2E)-N,N-dimethyl-3-phenylprop-2-enamide 72 96 3b (2E)-3-(4-methoxyphenyl)-N,N-dimethylprop-2-enamide 68 102 3c (2E)-3-(3,4-dimethoxyphenyl)-N,N-dimethylprop-2-enamide 76 88 3d (2E)-N,N-dimethyl-3-(3,4,5-trimethoxyphenyl)prop-2-enamide 60 127 3e (2E)-3-(1,3-benzodioxol-5-yl)-N,N-dimethylprop-2-enamide 66 118 3f (2E)-N,N-dimethyl-3-(2-nitrophenyl)prop-2-enamide 70 146 3g (2E)-3-(4-chlorophenyl)-N,N-dimethylprop-2-enamide 64 106 3h (2E)-N,N-dimethyl-3-(4-nitrophenyl)prop-2-enamide 70 176 3i (2E)-3-[4-(dimethylamino) phenyl]-N,N-dimethylprop-2-enamide 68 110 3j (2E)-3-(4-hydroxyphenyl)-N,N-dimethylprop-2-enamide 64 98 3k 2E)-N,N-diethyl-3-phenylprop-2-enamide 72 104 Spectroscopic data of representative compounds: The IR spectra were recorded on Perkin Elmer spectrometer using KBr Pelletes and HNMR spectra were recorded on Varian; USA makes Mercury plus 400 MHz, NMR Spectrometer by using CDCl3 with TMS as internal standard. 13CNMR spectra were recorded on Varian; USA makes Mercury plus 100 MHz, NMR Spectrometer by using CDCl3 with TMS as internal standard. The mass spectrum was recorded on Jeol make Accu TOF, Mass Spectrometer. Entry (3a)(2E)-N,N-dimethyl-3-phenylprop-2-enamide:Composition: C (75.52%), H (7.53%), N (7.98%), O (9.17%)IR (KBR) cm-1 3376,3277,3175,1664, 1656, 1609,1494,1272,1117,986,980, 940,792,760,690,640,530,480.HNMR (300MHz, CDCl3), ppm: 7.3-7.7 m (5H), 7.6 d (1H) (J= 15.5Hz), 6.48d (1H) (J= 15.5Hz), 3.14 s, (6H)13CNMR (100MHz, CDCl3), ppm:12.9, 41, 118.9, 126.4, 128.7, 135.2, 144, 162.8MS: m/e- 175 (M). Entry (3k)2E)-N,N-diethyl-3-phenylprop-2-enamide:Composition: C (76.80%), H (8.42%), N (6.90%), O (7.89%) IR (KBR) cm-1 3362,3177,3075,1660, 1652, 1590, 1410, 1252, 978, 960, 790,750,680,640,520,470. HNMR (300MHz, CDCl3), ppm: 7.2-7.3m (5H), 7.54 d (1H) (J= 17.5 Hz), 6.98 d (1H) (J= 17.5 Hz), 3.02 q (2H), 1.20 t (3H) MS: m/e= 204 (M). Conclusion The work described in this article follow the simple witting reaction mechanism and involves the use of SiOsolid support which gives the protocol of convenient and green synthesis. The reaction conditions may be employed for the synthesis of many other cinnamamide and related compounds. Acknowledgement The authors are thankful to Anuradha Engineering College, Chikhli,Dist-Buldana for providing all necessary facilities. Author is grateful to University Grants Comission for the award of MANF-JRF. Authors are also thankful to university of pune for providing instrumentation facilities for characterization of compounds. References Research Journal of Chemical Sciences ___________________________________________________________ISSN 2231-606XVol. 4(5), 56-58, May (2014) Res. J. Chem. Sci. 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