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Volume 2006
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Short Note

1-Nitro-3-[(phenylsulfonyl)methyl]benzene

by
Daniel G. Grohmann
and
Bruce A. Hathaway
*
Department of Chemistry, MS 6400, One University Plaza, Southeast Missouri State University, Cape Girardeau, MO, USA
*
Author to whom correspondence should be addressed.
Molbank 2006, 2006(5), M500; https://doi.org/10.3390/M500
Submission received: 6 July 2006 / Accepted: 1 August 2006 / Published: 1 September 2006
Versions Notes

In the course of our work to prepare inhibitors of the enzyme dihydrofolate reductase, we desired to prepare sulfone analogues of some previously reported sulfides [1, 2]. Therefore, we prepared the nitrosulfide 1 [1], and oxidized it with hydrogen peroxide in acetic acid [3, 4] to prepare the corresponding nitrosulfone, 2.
Molbank 2006 m500 i001
A mixture of 3-nitrobenzyl chloride (6.868 g, 40.03 mmoles), thiophenol (4.453 g, 40.42 mmoles), and potassium carbonate (5.585 g, 40.41 mmoles) were placed in a round bottom flask with 35 mL of acetone, and this mixture was refluxed for 16 hours. The potassium chloride that formed in the reaction was removed by vacuum filtration. The acetone was removed from the filtrate by using the rotovap. The product was purified by adding 40 mL of 5 M NaOH to the product in the flask. The nitro compound was extracted using 2 portions of ether and 1 portion of dichloromethane. The organic extracts were combined and dried with anhydrous magnesium sulfate. The organic solvents were removed with the rotavap to yield 9.027 g (36.80 mmoles) 1-nitro-3-(phenylthio)methyl]benzene, 1, as a dark-yellow viscous liquid. The percent yield for this reaction was 92%. This product was used without further purification in the next reaction.
1-nitro-3-(phenylthio)methyl]benzene, 1 (3.830 g, 15.61 mmoles), 12 mL of 30% hydrogen peroxide, and 30 mL of concentrated acetic acid were combined in a round bottom flask and refluxed for 24 hours. Initially, the reaction mixture was yellow, but after refluxing, a white solid became evident. The solution was allowed to cool, then the product was collected by suction filtration and allowed to dry. 3.266 g (11.78 mmoles) of 1-nitro-3-[(phenylsulfonyl)methyl]benzene, 2, was collected. The percent yield of this reaction was 75%.
Melting Point: 163-164 oC
IR (cm-1): 1520, 1351, 1319, 1297, 1280, 1112, 809, 730, 712, 695, 680, 671
1H-NMR (300 MHz, DMSO-d6): δ= 8.2 (1H, multiplet), 8.0 (1H, singlet), 7.7 (3H, multiplet), 7.6 (4H, multiplet), 4.9 (2H, singlet).
13C-NMR (75 MHz, DMSO-d6): δ= 147.3, 137.8, 137.6, 134.1, 131.0, 129.8, 129.2, 128.1, 125.5, 123.3, 59.4.
GC-MS [E.I., m/z (relative intensity)]: 136 (100), 90 (32), 89 (26), 177 (11), 277 (M+, 10), 155 (10), 77 (10).

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgment

The authors thank the Grants and Research Funding Committee of Southeast Missouri State University for financial support.

References

  1. Selassie, C.D.; Guo, Z.-r.; Hansch, C.; Khwaja, T. A.; Pentacost, S. A comparison of the Inhibition of Growth of Methotrexate-resistant and –Sensitive Leukemia Cells in Culture by Triazines. Evidence of a New Mechanism of Cell resistance to Methotrexate. J. Med. Chem 1982, 25, 157–161. [Google Scholar] [CrossRef] [PubMed]
  2. Hansch, C.; Hathaway, B.A.; Guo, Z.-r.; Selassie, C.D.; Dietrich, S.W.; Blaney, J.M.; Langridge, R.; Volz, K.W.; Kaufman, B.T. Crystallography, QSAR, and Molecular Graphics in a Comparative Analysis of the Inhibition of Dihydrofolate Reductase from Chicken Liver and L. casei by 4,6-Diamino-1,2-dihydro-2,2-dimethyl-1-(x-phenyl)-s-triazines. J. Med. Chem. 1984, 27, 129–143. [Google Scholar] [CrossRef] [PubMed]
  3. Rheinboldt, H.; Giesbrecht, E. The Configuration of Sulfoxides. Mixed Crystals of Sulfoxides and Sulfones. J. Amer. Chem. Soc. 1946, 68, 973–978. [Google Scholar] [CrossRef]
  4. Ongley, P.S. (Ed.) Organicum: Practical Handbook of Organic Chemistry; Addison-Wesley Publishing Company, Inc: Reading, MA, 1973; p. 637.

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MDPI and ACS Style

Grohmann, D.G.; Hathaway, B.A. 1-Nitro-3-[(phenylsulfonyl)methyl]benzene. Molbank 2006, 2006, M500. https://doi.org/10.3390/M500

AMA Style

Grohmann DG, Hathaway BA. 1-Nitro-3-[(phenylsulfonyl)methyl]benzene. Molbank. 2006; 2006(5):M500. https://doi.org/10.3390/M500

Chicago/Turabian Style

Grohmann, Daniel G., and Bruce A. Hathaway. 2006. "1-Nitro-3-[(phenylsulfonyl)methyl]benzene" Molbank 2006, no. 5: M500. https://doi.org/10.3390/M500

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