Next Article in Journal
One-pot Microwave-Assisted Synthesis of 1H-Phenanthro[9,10- d][1,2,3]triazole
Previous Article in Journal
Synthesis of 5,17,29- tri[(4-methyl-1-piperazinyl)methyl]- 11,23,35-tri-tert-butyl-37,39,41-trimethoxy-calix[6]arene
 
 
Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
Journals
Molbank
Volume 2008
Issue 3
10.3390/M576
molbank-logo
Submit to this Journal Review for this Journal Propose a Special Issue
► Article Menu

Article Menu

share Share announcement Help format_quote Cite question_answer Discuss in SciProfiles thumb_up
...
Endorse textsms
...
Comment
first_page
settings
Order Article Reprints
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Short Note

3-Dimethylaminomethylene-4-phenyl-1,3-dihydro-2H-1,5- benzodiazepin-2-one

by
Abdelouahhab El Rhazi
,
Abdesselam Baouid
*,
Said Elhazazi
,
Aicha Boudina
and
Mohamed Essaber
Laboratoire de Chimie Moléculaire, Equipe de Chimie des Hétérocycles et Valorisation des Extraits des Plantes, Département de Chimie, Faculté des Sciences-Semlalia, Université Cadi Ayyad, B.P 2390, 40001 Marrakech, Maroc
*
Author to whom correspondence should be addressed.
Molbank 2008, 2008(3), M576; https://doi.org/10.3390/M576
Submission received: 23 July 2008 / Accepted: 27 August 2008 / Published: 4 September 2008
Versions Notes

In this paper, we describe a facile and efficient method to prepare compound 2, which had been previously obtained by a Vilsmeier reaction using DMF/POCl3 [1]. We found that employment of dimethylformamide-dimethylacetal (DMF-DMA) affords the title compound in better purity and higher yield.
Molbank 2008 m576 i001
A mixture of 0.47 g (1.98 mmol) of 4-phenyl-1,3-dihydro-2H-1,5-benzodiazepin-2-one 1 [2,3] in 4.5 ml of dimethylformamide-dimethylacetal (DMF-DMA) was stirred at 100 °C for 4 hours and then cooled to room temperature. Filtration and washing with a little cold diethyl ether gave 0.46 g (75%) of 3-dimethylaminomethylene-4-phenyl-1,3-dihydro-2H-1,5-benzodiazepin-2-one 2. The product obtained was recrystallized from diethyl ether.
Melting point: 224-225 °C (Diethyl ether).
MS (m/z, %): 292 ([M+H]+, 100%).
1H NMR (CDCl3, 400 MHz), δ(ppm): 2.55 (s, 6H, (CH3)2N), 2.80 (s, 1H, NH), 7.40 (s, 1H, C=CH-N(CH3)2), 6.80-7.90 (m, 9H, H-Ar).
13C NMR (CDCl3, 100 MHz), δ(ppm): 43.50 (N(CH3)2), 98.02 (C-3), 121.47, 124.59, 127.34, 128.13, 128.67, 128.89, 130.65, 131.78, 141.86 (C-Ar), 151.18 (C=CH-N(CH3)2), 167.40 (C-4), 178.57 (C=O).

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

References

  1. Solomko, Z.F.; Proshkina, V.N.; Bozhanova, N.Ya.; Loban, S.V.; Babichenko, L.N. Vilsmeier reaction with 4-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-2-one. Khim. Geterosikl. Soedin. 1984, 223. [Google Scholar] [CrossRef]
  2. Ried, W.; Stahlhofen, P. Über heterocyclische siebenringsysteme, vii der reaktionsverlauf zwischen o-phenylendiamin und alkyliden-brenztraubensäuren. Chem. Ber. 1957, 90, 828. [Google Scholar] [CrossRef]
  3. Nardi, D.; Tajana, A.; Rossi, S. J. Heterocyclic compounds from 3,3-dimercapto-1-aryl-2-propen-1-ones. Note 1. 4-aryl-1,3-dihydro-2H-1,5-benzodiazepine-2-thiones. Heterocyc. Chem. 1973, 10, 815. [Google Scholar] [CrossRef]

Share and Cite

MDPI and ACS Style

El Rhazi, A.; Baouid, A.; Elhazazi, S.; Boudina, A.; Essaber, M. 3-Dimethylaminomethylene-4-phenyl-1,3-dihydro-2H-1,5- benzodiazepin-2-one. Molbank 2008, 2008, M576. https://doi.org/10.3390/M576

AMA Style

El Rhazi A, Baouid A, Elhazazi S, Boudina A, Essaber M. 3-Dimethylaminomethylene-4-phenyl-1,3-dihydro-2H-1,5- benzodiazepin-2-one. Molbank. 2008; 2008(3):M576. https://doi.org/10.3390/M576

Chicago/Turabian Style

El Rhazi, Abdelouahhab, Abdesselam Baouid, Said Elhazazi, Aicha Boudina, and Mohamed Essaber. 2008. "3-Dimethylaminomethylene-4-phenyl-1,3-dihydro-2H-1,5- benzodiazepin-2-one" Molbank 2008, no. 3: M576. https://doi.org/10.3390/M576

APA Style

El Rhazi, A., Baouid, A., Elhazazi, S., Boudina, A., & Essaber, M. (2008). 3-Dimethylaminomethylene-4-phenyl-1,3-dihydro-2H-1,5- benzodiazepin-2-one. Molbank, 2008(3), M576. https://doi.org/10.3390/M576

Note that from the first issue of 2016, this journal uses article numbers instead of page numbers. See further details here.

Article Metrics

Back to TopTop