Amberlyst A-15: Reusable catalyst for the synthesis
425
2.2 Typical procedure
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Mixture of benzyl (5 mmol), 4-Nitro- benzaldehyde
(5 mmol) and NH4OAc (5 mmol), aromatic amine
(5 mmol) and Amberlyst A-15 (350 mg) into 50 ml
borosil beaker and irradiated with microwaves. The
progress of reaction was monitored by TLC using
pet.ether and ethyl acetate (9:1). After completion of the
reaction the dichloromethane was added and the solid
Amberlyst-A-15 was filtered and dried at 80◦C and
used for its reusability. The organic layer was extracted
with H2O and dried by Na2SO4. The Organic layer
was removed under reduced pressure. Further, the crude
product was purified by column chromatography using
pet. ether and ethyl acetate (9:1) on silica gel gave the
product, 2-(4-Nitrophenyl)-4,5-diphenyl-1H-imidazole
and 2-(4-Nitrophenyl)-1,4,5-triphenyl-1H-imidazole.
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2.3 Spectroscopic data
2.3a 2(4-Nitrophenyl)-4,
5-diphenyl-1H-imidazole
(3h): IR KBr, (cm−1) 3400, 1580, 1515, 1335. H
NMR (CDCl3, 300 MHz): 7.1–7.6 (m, 10 H), 7.35 (d,
2 H, J = 10 Hz, 7.85 (d, 2 H, J = 10 Hz), 8.9 (bs, 1 H).
1
2.3b 2-(4-Nitrophenyl)-1,4,5-triphenyl-1H-imidazole
(5c): IR KBr, (cm−1) 1605, 1564, 1481, 1401. H
1
NMR(CDCl3, 300 MHz):7.17–7.84 (m, 19 H).
3. Conclusion
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In conclusion, we have developed a general and most
efficient one-pot multi-component reaction for the syn-
thesis of 2,4,5-trisubstituted-1H-imidazole and 1,2,4,5-
tetrasubstituted-1H-imidazole derivatives using het-
erogeneous and reusable catalysts Amberlyst A-15
under MW irradiation method which is environmentally
friendly.
16. Grimett M R In Comprehensive Heterocyclic Chemistry
II; Katritzky A R, Rees C W and Scriven E F 1996
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Acknowledgements
SSP thanks to University Grants Commission (UGC),
New Delhi for financial assistance, wide letter no. f-
47-503/08(WRO), dated 15.01.2009 and thanks are also
due to the Principal, Padmashri Vikhe Patil College
Pravaranagar for providing laboratory facilities.
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