Synthesis of 4,6-bis(thiomorpholin-4-ylmethyl)-1,2,3-benzenetriol

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 4,6-bis(thiomorpholin-4-ylmethyl)-1,2,3-benzenetriol by A. Ma. Velázquez 1, L. Torres 1, R. González 1, A. Valencia 1, I. Martínez 1, A. Pecina 1, I. Menconi 1, L. Martínez 1, A. Ramírez 1, R. Hernández 1, R. López-Castañares 2, O. Olvera-Neria 3 and E. Angeles 1,* 1 Facultad de Estudios Superiores Cuautitlán, Universidad Nacional Autónoma de México 2 Facultad de Química de la UAEM 3 Instituto de Ciencias Básicas e Ingenieria, Universidad Autónoma del Estado de Hidalgo, Mexico * Author to whom correspondence should be addressed. Molbank 2005, 2005(1), M399; https://doi.org/10.3390/M399 Received: 2 April 2004 / Accepted: 31 May 2004 / Published: 1 July 2005 Download Download PDF Download PDF with Cover Download XML Download Epub Download Supplementary Material Versions Notes 4,6-bis(thiomorpholin-4-ylmethyl)-1,2,3-benzenetriol (2) was prepared from pyrogalol (1) and thiomorpholine and formaldehyde (37%) in methanol as solvent . A solution of methanol (50 mL) and pyrogalol (1.24g, 9.83mmol) 1 was prepared, after that a solution of thiomorpholine (2.0g, 20.70 mmol) and formaldehyde (2.0 mL, 24.6 mmol) in methanol were added at rt. When the addition was completed, the reaction mixture was stirred at room temperature for 10 minutes and one red solid was formed and it was isolated for filtration and recristalizaded from ethanol (2.90g, 83% yield).Melting Point: 181-183 C° (ethanol, uncorrected)IR (CHCl3 film, cm-1): 3429 (O-H); 3065 (Csp2-H Ar); 2872 (Csp3-H).1H-NMR (300 MHz; CDCl3): δ= 8.40 (3H, s, OH); 6.20 (1H, s); 3.61 (4H, s, Ar-CH2); 2.81 (8H, m, -S-CH2-); 2.72 (8H, m, -N-CH2-); 1.27.13C-NMR (75 MHz; CDCl3): δ= 144.8 (C); 132.51 (C); 118.42 (CH); 111.74(C); 61.63 (Ar-CH2); 54.22 (-N-CH2-); 27.81 (-S-CH2-).MS (FAB; m/z, %): 357 (10%); 254(100%); 102(91).Elemental Analysis: Calculated for C16H24N2O3S2: C, 53.91%; H, 6.79%; N, 7.86%; O, 13.46%; S,17.99%. Found: C, 53.90%; H, 6.74%; N, 57.91%; O, 13.37%; S, 18.02%. Supplementary materialsSupplementary File 1Supplementary File 2Supplementary File 3AcknowledgementsThe authors wish to acknowledge to PAPIIT/UNAM Projects No IN205902 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.ReferencesArtico, M.; Mai, A.; Sbardella, G.; Massa, S.; Lampis, G.; Deidda, D.; Pompei, R. Bioorganic & Medicinal Chemistry Letters 1999, 8, 1493–1498.Biava, M.; Fioravanti, R.; Porretta, G.C.; Deidda, D.; Maullu, C.; Pompei, R. Bioorganic & Medicinal Chemistry Letters 1999, 9, 2083–2988.Mai, A.; Sbardella, G.; Artico, M.; Massa, S.; Lampis, G.; Deidda, D.; Pompei, R. Medicinal Chemistry Research 1999, 9, 149–161. © 2005 MDPI. All rights reserved. Share and Cite MDPI and ACS Style Velázquez, A.M.; Torres, L.; González, R.; Valencia, A.; Martínez, I.; Pecina, A.; Menconi, I.; Martínez, L.; Ramírez, A.; Hernández, R.; López-Castañares, R.; Olvera-Neria, O.; Angeles, E. Synthesis of 4,6-bis(thiomorpholin-4-ylmethyl)-1,2,3-benzenetriol. Molbank 2005, 2005, M399. https://doi.org/10.3390/M399 AMA Style Velázquez AM, Torres L, González R, Valencia A, Martínez I, Pecina A, Menconi I, Martínez L, Ramírez A, Hernández R, López-Castañares R, Olvera-Neria O, Angeles E. Synthesis of 4,6-bis(thiomorpholin-4-ylmethyl)-1,2,3-benzenetriol. Molbank. 2005; 2005(1):M399. https://doi.org/10.3390/M399 Chicago/Turabian Style Velázquez, A. Ma., L. Torres, R. González, A. Valencia, I. Martínez, A. Pecina, I. Menconi, L. Martínez, A. Ramírez, R. Hernández, R. López-Castañares, O. Olvera-Neria, and E. Angeles. 2005. "Synthesis of 4,6-bis(thiomorpholin-4-ylmethyl)-1,2,3-benzenetriol" Molbank 2005, no. 1: M399. https://doi.org/10.3390/M399 Find Other Styles Note that from the first issue of 2016, MDPI journals use 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.