4,5-Dimethoxy-2-(4-methylbenzoyl)-1-(4-methylphenylsulfonylamido)benzene
Sergey K. Smirnov, Artem S. Dmitriyev and Irina V. Lodina
Research Laboratory of Furan Chemistry, Kuban State Technological University, Moskovskaya st. 2, Krasnodar, 350072, Russia, E-mail: [email protected], E-mail: [email protected].
Received: 19 November 2000 / Accepted: 15 December 2000 / Published: 25 March 2001
For this synthesis, we propose a modification of the reaction procedure described in [1]. To a warm solution of amine 1 (2.06 g, 8 mmol) in acetone (70 mL), p-TsCl (3.5 g, 1.8 mmol) was added and the reaction mixture was heated to dissolve p-TsCl. After that, water (7 mL) and NaHCO3 (1.70 g, 20 mmol) were added. The mixture was heated to reflux for 5 days. In order to separate product 2, H2O (25 mL) was added and the reaction mixture was concentrated to half its volume. The crystallization from acetone with charcoal gave titled compound (1.8 g, 53 %) as pale yellow crystals. The filtrate after separating compound 2 was diluted with water and extracted with ethyl acetate. The extracts were dried over Na2SO4, and solvent was evaporated. The residue was worked up as described above yielding the additional amount of the compound 2 (0.92 g, 27 %).
Total yield of compound 2 is 2.72 g (80 %).
M.p. 218 °C (acetone).
IR (Nujol): 1620 (C=O), 3280 (NH).
1H NMR (CDCl3, 80 MHz): 2.17 (3H, s, CH3); 2,40 (3H , s, CH3); 3.67 (3H, s, OCH3); 3.97 (3H, s, OCH3); 6.73 (1H, s, HAr); 6.93 (2H, d, J=8.8 Hz, HTs); 7.17 (4H, s, HAr); 7.30 (1H, s, HAr); 7.47 (2H, d, J=8.8 Hz, HTs); 10.07 (1H, s, NH)
Anal. calc. for C23H23NO5S: C 64.94, H 5.41, N 3.29; found C 65.09, H 5,50, N 3.19.
Reference
| 1. | Tietze, L.F.; Eicher, T. Reactionen und Synthesen im organisch-chemischen Praktikum und Forschungslaboratorium Georg Thieme Verlag Stuttgart, New York, 1991. |
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