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Ugi Reaction. Part VII; N,N'-(4,4'-oxybis(4,1-phenylene))bis(2-chloro-N-(2-(cyclohexylamino)-2-oxo-1-phenylethyl)acetamide)

SyntheticPage 798
DOI: 10.1039/SP798
Submitted Aug 19, 2015, published Aug 25, 2015
Sirin Gulten (siringulten@hotmail.com)
Reaction Scheme: <img src="/images/empty.gif" alt="" /><img src="/images/empty.gif" alt="" />Ugi Reaction<img src="/images/empty.gif" alt="" /><img src="/images/empty.gif" alt="" />. Part VII

Chemicals Used

4,4'-Diaminodiphenylether (Merck)

Benzaldehyde (Acros Organics)

Cyclohexyl isocyanide (Merck)

Chloroacetic acid (Fluka)

MeOH (Riedel-de Haën)

 

Procedure

A solution of 4,4'-diaminodiphenylether (0.998 mmol, 200 mg) in MeOH (7 mL) was treated with benzaldehyde (1.99 mmol, 0.20 mL), a solution of cyclohexyl isocyanide (1.99 mmol, 0.24 mL) in MeOH (3 mL), and chloroacetic acid (1.99 mmol, 188 mg) in the order given. The reaction mixture was stirred at room temperature for 28 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 (720 mg, 92%). m.p. 192-195oC, Rf(80%EtOAc/n-hexane): 0.81

Author's Comments

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

Data

IR-ATR: 3263, 3088, 3067, 2929, 2854, 1677, 1646, 699 cm-1; 1H NMR (400MHz, CDCl3): δ= 7.28-7.18 (14H, m, CHAr), 7.1 (4H, d, J=7.3 Hz, CHAr), 6.01 (2H, s, 2PhCH), 5.45 (2H, d, J=7.8 Hz, 2NH), 3.86-3.81 (6H, m, 2CH cyclohexyl and 2CH2Cl), 1.93-1.87 (4H, m, 2CH2 cyclohexyl), 1.66-1.50 (8H, m, 2CH2 cyclohexyl), 1.32-0.84 (8H, m, 4CH2 cyclohexyl) ppm; 13C NMR (100MHz, CDCl3): δ= 168.18 (Cq), 166.97 (Cq), 156.64 (Cq), 133.95 (Cq), 133.89 (Cq), 132.27 (CHAr), 130.51 (CHAr), 128.89 (CHAr), 128.65 (CHAr), 119.14 (CHAr), 65.47 (CH), 49.04 (CH), 42.58 (CH2), 32.91 (CH2), 32.86 (CH2), 25.52 (CH2), 24.91 (CH2), 24.81 (CH2) ppm.

 

Lead Reference

Marcaccini, S.; Pepino, R.; Pozo, M.C. Tetrahedron Lett. 2001, 42, 2727. doi: 10.1016/S0040-4039(01)00232.

Other References

Martins, M.B.; Carvalho, I. Tetrahedron, 2007, 63, 9923. doi:10.1016/j.tet.2007.04.105.

 

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 1 (Proton NMR 1.png)
Proton NMR 2 (Proton NMR 2.png)
Carbon NMR (Carbon NMR.png)

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