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Volumn 28, Issue 6, 2007, Pages 913-914

Synthesis of 2-arylsubstituted imidazolone derivatives

Author keywords

2 Arylimidazolone; Amino acids; C C bond formation; Carbodiimide

Indexed keywords

EID: 34250838599 PISSN: 02532964 EISSN: 12295949 Source Type: Journal
DOI: 10.5012/bkcs.2007.28.6.913 Document Type: Article

Times cited : (4)

References (27)

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27
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- General procedure for carbodiimide (2a, To a suspension of L-phenylalanine ethyl ester HCl salt 1a (10.0 g, 43.5 mmol) in 200 mL of dried CH2Cl2 was added phenylisocyanate (5.7 g, 47.9 mmol, 1.1 equiv, followed by an addition of triethylamine (5.3 g, 52.2 mmol, 1.2 equiv, at 0°C. The reaction mixture was stirred for 5 hr at room temperature and treated with 100 mL of water. The mixture was extracted with CH2Cl2. The combined extracts were dried over anhydrous MgSO4, filtered, and concentrated to give solid, which was washed with petroleum ether and dried in vacuo to provide the desired urea compound 2a (10.6 g, 82, as a white solid: 1H NMR (CDCl3, 300 MHz) δ7.30-7.06 (m, 10H, Ph, 6.84 (s, 1H, Ph-NH, 5.56 (1H, d, J, 7.9 Hz, CONH, 4.84 (1H, m, CHCO2Et, 4.18 (2H, q, J, 7.2 Hz, CHCO2CH2CH3, 3.14-3.05 2H, m, PhCH
- +).

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