Synthesis Of 4-Bromo-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-bromo-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), M548; https://doi.org/10.3390/M548 Received: 19 January 2007 / Accepted: 24 February 2007 / Published: 23 August 2007 Download Download PDF Download PDF with Cover Download XML Download Epub Download Supplementary Material Versions Notes Keywords: 4-bromophenol; thiomorpholine; IR 4-bromo-2-thiomorpholin-4-ylmethyl-1-phenol (2) was prepared from 4-bromophenol (1) and thiomorpholine and formaldehyde (2 eq.) and 1 eq. of thiomorpholine. 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 7 minutes, the reaction was completed. The mixture was chromatographed on silica gel using solvent gradient hexane/ethyl acetate. Yield 63%Melting point: 130-132 °C (hexane/ethylacetate, uncorrected).IR (n cm-1; CHCl3 film): 3520 (O-H), 3010 (Csp2-H Ar), 2985 (Csp3-H).1H-NMR (200 MHz; CDCl3; Me4Si, δH): 10.69 (1H, s, OH), 7.26 ( 1H, dd, J=8.8Hz, J=2.4Hz), 7.082 (1H, d, J=2.4Hz), 6.70 (1H, d, J=8.8Hz), 3.67 (2H, s, Ar-CH2), 2.81 (4H, m, -S-CH2- ), 2.74 (4H, m, -N-CH2-).13C-NMR (50 MHz; CDCl3; δC): 156.7 (C), 131.61 (CH), 131.25 (CH), 122.76 (C), 117.9(CH), 110.88 (C), 61.66 (Ar-CH2), 54.36 (-N-CH2-), 27.84 (-S-CH2-).FAB-MS m/z (rel%) (M+1): 288(53%), 221, 135Elemental Analysis: Calculated for C11H14BrONS (287): C 45.99 %, H 4.87 %, N 4.87 %, O 5.57 %, S 11.15 %, Br 25.52, found : C 46.07 %, H 4.98 %, N 4.81 %, O 5.6 %, S 11.23 %, Br 25.34%. 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.; et al. Synthesis of 4-bromo-2-thiomorpholin-4-ylmethyl-1-phenol. Molbank 2007, 2007, M548. https://doi.org/10.3390/M548 AMA Style Velázquez AM, Torres LA, González R, Valencia A, Díaz-Barriga S, Menconi I, Martínez L, Ramírez A, Martínez I, Camacho B, et al. Synthesis of 4-bromo-2-thiomorpholin-4-ylmethyl-1-phenol. Molbank. 2007; 2007(3):M548. https://doi.org/10.3390/M548 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, and et al. 2007. "Synthesis of 4-bromo-2-thiomorpholin-4-ylmethyl-1-phenol" Molbank 2007, no. 3: M548. https://doi.org/10.3390/M548 Find Other Styles Note that from the first issue of 2016, this journal uses article numbers instead of page numbers. See further details here. Article Metrics No No Article Access Statistics For more information on the journal statistics, click here. Multiple requests from the same IP address are counted as one view.