Synthesis of 5,5-diphenyl-3-(methylthiomethyl)hydantoin and 5,5-diphenyl-3-(methysulfonylomethyl)hydantoin
Institute of Organic Chemistry and Technology, Cracow University of Technology, ul. Warszawska 24, PL-31155 Kraków, Poland
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Molbank 2006, 2006(3), M480; https://doi.org/10.3390/M480
Submission received: 9 October 2005
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Accepted: 18 October 2005
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Published: 31 March 2006
In view of potential biological activity of 5,5-diphenylhydantoin derivatives (psychotropic agents)[1,2,3] we obtained 5,5-diphenyl-3-(methylthiomethyl)hydantoin (2) in reaction of 5,5-diphenylhydantoin (1) with DMSO and subsequently undergo its oxidation reaction to 5,5-diphenyl-3-(methysulfonylomethyl)hydantoin (3) [4].
5,5-diphenyl-3-(methylthiomethyl)hydantoin (2)
A solution of 5,5-diphenylhydantoin (1) (commercial product) (17.5 g, 0.069 mol) in dimethylsulfoxide (DMSO, 350ml) was refluxed for 16 hrs, then cooled and poured into water (350 ml). The precipitated solid was filtered off, washed with water and dried. After two recrystalizations from methanol 5,5-diphenyl-3-methylthiomethylhydantoin (2, 20.5 g, 94.6%) was obtained as colorless needles.
Melting point: 124-131°C.
1H NMR (DMSO-d6, 80 MHz): δ= 9.80 (s, 1H, NH), 7.40 (s,10H, Ph), 4.56 (s, 2H, CH2), 2.15 (s, 3H, CH3).
IR (KBr, cm-1): 3270 (NH), 1780 (C=O).
MS (70eV) m/z (%): 312 (100), 297 (17.9), 265 (42.0), 251(67.9), 237 (100).
Elemental Analysis: Calculated for C17H16N2O2S (312.39): C 65.40, H 5.10, N 9.00; found C 65.20, H 5.10, N 8.80.
5,5-diphenyl-3-(methysulfonylomethyl)hydantoin (3)
A solution of 5,5-diphenyl-3-(methylthiomethyl)hydantoin (2) (5.0 g, 0.016mol), glacial acetic acid (100 ml) and 30% H2O2 (100 ml) was allowed to stand at room temperature for 20 hrs. Then the solution was neutralized with 50% NaOH to pH 7. The precipitated solid was filtered off, washed several times with water and dried. 5,5-Diphenyl-3-(methylsulfonyl-methyl)hydantoin (3, 5.1 g, 95.3%). After recrystallization from water-methanol (7:3) mixture, compound 3 as colorless needles (4.35 g, 81.3%) was obtained.
Melting point: 196-197°C
1H NMR (DMSO-d6, 80 MHz): δ= 9.98 (s, 1H, NH), 7.39 (s, 10H, Ph), 4.97 (s, 2H, CH2), 3.15 (s, 3H, CH3).
IR (KBr, cm-1): 3365 (NH), 1785 and 1734 (C=O), 1140 (SO2).
Elemental Analysis: Calculated for C17H16N2O4S (344.39): C 59.30, H 4.60, N 8.10; found C 59.10, H 4.60, N 8.00.
Supplementary materials
Supplementary File 1Supplementary File 2Supplementary File 3Supplementary File 4Supplementary File 5Supplementary File 6References
- Foye, W.O. Principles of Medicinal Chemistry; Lea & Febiger: Philadelphia, 1989. [Google Scholar]
- Avendano-Lopez, C.; Gonzalez-Trigo, G. Advances in Heterocyclic Chemistry; Katrizky, A.R., Ed.; Academic Press, Inc.: Orlando, 1985; Volume 38, chapter 4. [Google Scholar]
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- Czuba, W.; Grzegożek, M.; Kaniewska, A.; Nowak, K.; Poradowska, H.; Sędzik-Hibner, D.; Szpakiewicz, B.; Walkowicz, C. Pol. J. Chem. 1986, 60, 459.
- Sample Availability: Available from MDPI.
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MDPI and ACS Style
Grzegożek, M.; Nowak, K.; Szpakiewicz, B. Synthesis of 5,5-diphenyl-3-(methylthiomethyl)hydantoin and 5,5-diphenyl-3-(methysulfonylomethyl)hydantoin. Molbank 2006, 2006, M480. https://doi.org/10.3390/M480
AMA Style
Grzegożek M, Nowak K, Szpakiewicz B. Synthesis of 5,5-diphenyl-3-(methylthiomethyl)hydantoin and 5,5-diphenyl-3-(methysulfonylomethyl)hydantoin. Molbank. 2006; 2006(3):M480. https://doi.org/10.3390/M480
Chicago/Turabian StyleGrzegożek, Maria, Krystyna Nowak, and Barbara Szpakiewicz. 2006. "Synthesis of 5,5-diphenyl-3-(methylthiomethyl)hydantoin and 5,5-diphenyl-3-(methysulfonylomethyl)hydantoin" Molbank 2006, no. 3: M480. https://doi.org/10.3390/M480
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