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Short 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
Submission received: 28 August 1999 / Accepted: 2 September 1999 / Published: 8 October 1999
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Versions Notes
Molecules 04 m107 i001
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°C
IR (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 materials

Supplementary File 1Supplementary File 2

Acknowledgement 

Financial support by the Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung (project no. 20-41857.94) is gratefully acknowledged.

References

  1. Hubmann, 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.

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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

APA Style

Hubmann, D., & Séquin, U. (1999). N-(3-Phenyl-2-propinoyl)benzamide. Molecules, 4(10), M107. https://doi.org/10.3390/M107

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