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Ugi Reaction. Part IV; N,N'-(4,4'-(ethane-1,2-diyl)bis(4,1-phenylene))bis(2,2,2-trichloro-N-(2-(cyclohexylamino)-2-oxo-1-phenylethyl)acetamide)

SyntheticPage 795
DOI: 10.1039/SP795
Submitted Aug 19, 2015, published Aug 25, 2015
Sirin Gulten (siringulten@hotmail.com)
Reaction Scheme: <img src="/images/empty.gif" alt="" />Ugi Reaction<img src="/images/empty.gif" alt="" />. Part IV

Chemicals Used

4,4'-Diaminobibenzyl (Fluka)

Benzaldehyde (Acros Organics)

Cyclohexyl isocyanide (Merck)

Trichloroacetic acid (Riedel-de Haën)

MeOH(Riedel-de Haën)

 

Procedure

A solution of 4,4'-diaminobibenzyl (0.94 mmol, 200 mg) in MeOH (7 mL) was treated with benzaldehyde (1.88 mmol,0.19 mL), a solution of cyclohexyl isocyanide (1.88 mmol, 0.23 mL) in MeOH (3 mL), and trichloroacetic acid (1.88 mmol, 310 mg) in the order given. The reaction mixture was stirred at room temperature for 24 hours, and then filtered. The precipitate was washed with first Et2O and then with n-hexane to remove unreacted reagents or by-products and dried to give white Ugi adduct (630 mg, 72%). m.p. 227-230oC, Rf(50%EtOAc/n-hexane): 0.77

Author's Comments

The author thanks to NMR analysis Laboratory of Çanakkale Onsekiz Mart University for recording NMR spectra.

Data

IR-ATR: 3268, 3063, 3034, 2927, 2854, 1690, 1649, 698 cm-1; 1H NMR (400MHz, CDCl3): δ= 7.3-7.16 (14H, m, CHAr), 7.1 (4H, d, J=8.2 Hz, CHAr), 5.97 (2H, s, 2PhCH), 5.23 (2H, d, J=7.8 Hz, 2NH), 3.79-3.77 (2H, m, 2CH cyclohexyl), 2.71 (4H, s, CH2CH2), 1.94-1.81 (4H, m, 2CH2 cyclohexyl), 1.64-1.58 (4H, m, 2CH2 cyclohexyl), 1.34-1.31 (4H, m, 2CH2 cyclohexyl), 1.31-1.28 (8H, m, 4CH2 cyclohexyl) ppm; 13C NMR (100MHz, CDCl3): δ = 167.43 (Cq), 161.01 (Cq), 141.71 (Cq), 136.28 (Cq), 133.47 (Cq), 132.24 (CHAr), 130.71 (CHAr), 129.00 (CHAr), 128.61 (CHAr), 128.23 (CHAr), 127.93 (CHAr), 93.15 (Cq), 70.11 (CH), 49.04 (CH), 37.48 (CH2), 32.91 (CH2), 32.88 (CH2), 25.52 (CH2), 24.94 (CH2), 24.83 (CH2) ppm.

 

Lead Reference

Ignacio, J. M.; Macho, S.; Marcaccini, S.; Pepino, R.; Torroba, T. Synlett, 2005, 20, 3051. doi:10.1055/s-2005-922745

Supplementary Information

e.g. Actual NMR spectra (as images or jdx files for interactive spectra), photographs of apparatus, TLC’s or crystals or videos. Please contact the ChemSpider team (ChemSpider-at-rsc.org) for help with this.
Proton NMR (Proton NMR.png)
Carbon NMR (Carbon NMR.png)

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Keywords: addition, aldehydes, aromatics/arenes, carboxylic acids, elimination, Multicomponent reaction, nucleophilic, peptides, substitution