Synthesis Of 4-Methoxy-2-Thiomorpholin-4-Ylmethyl-1-Phenol

first_page settings Order Article Reprints Font Type: Arial Georgia Verdana Font Size: Aa Aa Aa Line Spacing:    Column Width:    Background: Open AccessShort Note Synthesis of 4-methoxy-2-thiomorpholin-4-ylmethyl-1-phenol by Ana María Velázquez 1, Luis Alberto Torres 1, Raúl González 1, Alvaro Valencia 1, Sandra Díaz-Barriga 1, Italo Menconi 1, Luisa Martínez 1, Alberto Ramírez 1, Ignacio Martínez 1, Brígida Camacho 1, Rafael López-Castañares 2 and Enrique Angeles 1,* 1 Facultad de Estudios Superiores Cuautitlán, Universidad Nacional Autónoma de México, México 2 Facultad de Química de la UAEM, Universidad Autónoma del Estado de México * Author to whom correspondence should be addressed. Molbank 2007, 2007(3), M547; https://doi.org/10.3390/M547 Received: 19 January 2007 / Accepted: 23 February 2007 / Published: 23 August 2007 Download Download PDF Download PDF with Cover Download XML Download Epub Download Supplementary Material Versions Notes Keywords: 4-methoxyphenol; thiomorpholine; IR Infrared light activation as a non-conventional energy source has become an important method that can be used to carry out a wide range of reactions with short reaction times and high yields. Indeed, infrared light heating rapidly increases temperature in absence of the solvent and leads to a uniform energy transfer to the reactants of the chemical reaction. This method does not involve toxic materials, resulting in an economic process, which has clear advantages as an environmentally friendly, solvent-free alternative in organic synthesis. In our experience and, according to the reports in the literature, when the reaction mixtures were refluxed using ethanol as solvent in the absence of infrared light irradiation, the reaction times were in the range of 1–100 hours and the yields were lower.4-methoxy-2-thiomorpholin-4-ylmethyl-1-phenol (2) was prepared from 4-methoxyphenol (1), 1 eq. of thiomorpholine and 2 eq. of formaldehyde. They were mixed in a round flask fitted with a condenser. The mixture was irradiated with infrared light using a medicinal infrared lamp (250 Watts) and the reaction was monitored by tlc, and after 8 minutes, the reaction was completed. The mixture was chromatographed on silica gel using solvent gradient hexane/ethyl acetate. Yield 76%Melting point: 102-104 °C (ethylacetate, uncorrected).IR (n cm-1; CHCl3 film): 3452 (O-H), 3010 (Csp2-H Ar), 2985 (Csp3-H).1H-NMR (200 MHz; CDCl3; Me4Si, δH): 10.08 (1H, s, OH), 7.74 ( 2H, m), 6.55 (1H, m), 3.73 (3H, s), 3.66 (2H, s, Ar-CH2), 2.82 (4H, m, -S-CH2- ), 2.71 (4H, m, -N-CH2-).13C-NMR (50 MHz; CDCl3; δC): 152.5 (C), 151.2 (C), 122.52 (C), 116.4 (CH), 111.5 (CH), 113.6(CH), 62.3 (Ar-CH2), 55.66 (CH3), 54.36 (-N-CH2-), 27.82 (-S-CH2-).FAB-MS m/z (rel%) (M+1): 240(25%), 215, 180, 154.Elemental Analysis: Calculated for C12H17O2NS (239): C 60.22 %, H 7.16 %, N 5.85 %, O 13.37 %, S 13.40 %, found : C 60.49 %, H 7.54 %, N 5.49 %, O 13.05 %, S 13.22 %. Supplementary MaterialsSupplementary File 1Supplementary File 2Supplementary File 3AcknowledgementsThe authors wish to acknowledge to PAPIIT/UNAM Projects No IN213606 and IN207705 and ALPHARMA SA de CV, by partially support this work. We would like to thank C.Barajas, F.Sotres, P.García, D.Jiménez from FESC-UNAM and Rosa I.del Villar M., Oscar Yañez and Georgina Duarte from USAI-UNAM for their skillful technical assistance and DGSCA-UNAM for their support. As a part of Project Cátedra Química Medicinal of FESC-UNAM.ReferencesVelázquez, A.Ma.; Torres, L.A.; Díaz, G.; Ramírez, A.; Hernández, R.; Santillán, H.; Martínez, L.; Martínez, I.; Díaz-Barriga, S.; Abrego, V.; Balboa, M.A.; Camacho, B.; López-Castañares, R.; Dueñas-González, A.; Cabrera, G.; Angeles, E. ARKIVOC 2006, 2, 150–161.Biava, M.; Fioravanti, R.; Porretta, G.C.; Deidda, D.; Maullu, C.; Pompei, M. Biorg. & Med. Chem. Lett. 1999, 9, 2083–2985.Teipel, S.; Griesar, K.; Haase, W.; Krebs, B. Inorganic Chemistry 1994, 33, 456–464.Hodgkin, J.H. Aust. J. Chem. 1984, 37, 2371–2378. © 2007 by MDPI (http://www.mdpi.org/). Reproduction is permitted for noncommercial purposes. Share and Cite MDPI and ACS Style Velázquez, A.M.; Torres, L.A.; González, R.; Valencia, A.; Díaz-Barriga, S.; Menconi, I.; Martínez, L.; Ramírez, A.; Martínez, I.; Camacho, B.; López-Castañares, R.; Angeles, E. Synthesis of 4-methoxy-2-thiomorpholin-4-ylmethyl-1-phenol. Molbank 2007, 2007, M547. https://doi.org/10.3390/M547 AMA Style Velázquez AM, Torres LA, González R, Valencia A, Díaz-Barriga S, Menconi I, Martínez L, Ramírez A, Martínez I, Camacho B, López-Castañares R, Angeles E. Synthesis of 4-methoxy-2-thiomorpholin-4-ylmethyl-1-phenol. Molbank. 2007; 2007(3):M547. https://doi.org/10.3390/M547 Chicago/Turabian Style Velázquez, Ana María, Luis Alberto Torres, Raúl González, Alvaro Valencia, Sandra Díaz-Barriga, Italo Menconi, Luisa Martínez, Alberto Ramírez, Ignacio Martínez, Brígida Camacho, Rafael López-Castañares, and Enrique Angeles. 2007. 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