N-(3-Phenyl-2-propinoyl)benzamide

Abstract

first_page settings Order Article Reprints Font Type: Arial Georgia Verdana Font Size: Aa Aa Aa Line Spacing:    Column Width:    Background: Open AccessShort Note N-(3-Phenyl-2-propinoyl)benzamide by Dieter Hubmann and Urs Séquin * Institut für Organische Chemie der Universität Basel, St. Johanns-Ring 19. CH-4056 Basel, Switzerland * Author to whom correspondence should be addressed. Molecules 1999, 4(10), M107; https://doi.org/10.3390/M107 Received: 28 August 1999 / Accepted: 2 September 1999 / Published: 8 October 1999 (This article belongs to the Section Molbank Section of Molecules, 1997-2001) Download Download PDF Download PDF with Cover Download XML Download Epub Download Supplementary Material Versions Notes During the synthesis of a series of carboximides using acyl isocyanates [1], the title compound 3 was synthesised as a model compound from benzoyl isocyanate (1) and lithium phenylacetylide (2).To benzoyl isocyanate (342 ml, 2.72 mmol, Aldrich) in tetrahydrofuran (8 ml), a solution of lithium phenylacetylide in tetrahydrofuran (2.72 ml, 1.0 M, 2.72 mmol, Aldrich) was added under argon at -15°C, and the mixture stirred for 90 min at -15°C. Dilute hydrochloric acid (20 ml, 2 M) was added and the mixture was extracted three times with dichloromethane (20 ml each). The combined organic layers were dried (Na2SO4), filtered, and the solvent removed in vacuo. The residue was chromatographed on SiO2 (60 g, dichloromethane) to give 414 mg (61%) of 3 as yellowish needles.Yellowish nedles, m.p. 110-112°CIR (KBr): 3266; 3079; 2235; 2192; 1713; 1648; 1459; 1325; 1238; 761; 694.1H-NMR (300 MHz, CDCl3): 10.02 (s br, 1H, NH); 7.97 (d, J = 7.1, 2H, H-C(2''), H-C(6'')); 7.63 - 7.30 (m, 8H, H-C(3''), H-C(4''), H-C(5''), H-C(2'), H-C(3'), H-C(4'), H-C(5'), H-C(6')).13C-NMR (75 MHz, CDCl3): 165.1 (s, C6H5-C=O); 153.3 (s, C(1)); 133.2 (d, C(4'')); 132.9 (d, C(2'), C(6')); 131.9 (s, C(1'')); 130.7 (d, C(4')); 128.6, 128.3, 127.9 (3d, C(2''), C(3''), C(5''), C(6''), C(3'), C(5')); 119.5 (s, C(1')); 93.0 (s, C(3)); 82.9 (s, C(2)).EI-MS (70 eV): 249 (5, M+); 221 (8); 178 (18); 129 (16, [C6H5C°CC=O]+); 118 (100); 105 (40, [C6H5CO]+); 90 (39); 77 (21, [C6H5]+); 63 (6); 51 (11).CI-MS (NH3): 250 (100, [M+H]+); 118 (10).Anal. Calcd for C16H11NO2 (249.27): C 77.10, H 4.45, N 5.62, O 12.84; Found: C 76.92, H 4.60, N 5.59, O 12.74. Supplementary materialsSupplementary File 1Supplementary File 2Acknowledgement Financial support by the Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung (project no. 20-41857.94) is gratefully acknowledged.ReferencesHubmann, D.; Liechti, C.; Trinks, U.; Traxler, P.; Séquin, U. Synthesis of N-Phenylpyrrole Carboximides. Molecules 1999, 4, 151–158. [Google Scholar] [CrossRef] Sample availability: available from the authors and from MDPI. MDPI ID 17925. © 1999 MDPI. All rights reserved. Molecules website www.mdpi.org/molecules/ Share and Cite MDPI and ACS Style Hubmann, D.; Séquin, U. N-(3-Phenyl-2-propinoyl)benzamide. Molecules 1999, 4, M107. https://doi.org/10.3390/M107 AMA Style Hubmann D, Séquin U. N-(3-Phenyl-2-propinoyl)benzamide. Molecules. 1999; 4(10):M107. https://doi.org/10.3390/M107 Chicago/Turabian Style Hubmann, Dieter, and Urs Séquin. 1999. "N-(3-Phenyl-2-propinoyl)benzamide" Molecules 4, no. 10: M107. https://doi.org/10.3390/M107 Find Other Styles Note that from the first issue of 2016, this journal uses article numbers instead of page numbers. See further details here. Article Metrics No No Article Access Statistics For more information on the journal statistics, click here. Multiple requests from the same IP address are counted as one view.