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Short 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
Submission received: 19 January 2007 / Accepted: 24 February 2007 / Published: 23 August 2007
Versions Notes

Molbank 2007 m548 i001
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, 135
Elemental 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 Materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgements

The 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.

References

  1. Velázquez, 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.
  2. Biava, M.; Fioravanti, R.; Porretta, G.C.; Deidda, D.; Maullu, C.; Pompei, M. Biorg. & Med. Chem. Lett. 1999, 9, 2083–2985.
  3. Teipel, S.; Griesar, K.; Haase, W.; Krebs, B. Inorganic Chemistry 1994, 33, 456–464.
  4. Hodgkin, J.H. Aust. J. Chem. 1984, 37, 2371–2378.

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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

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