Molbank 2007, M548

http://www.mdpi.org/molbank/

Synthesis of 4-bromo-2-thiomorpholin-4-ylmethyl-1-phenol

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. E-mail: [email protected]

Received: 19 January 2007 / Accepted: 24 February 2007 / Published: 23 August 2007

Keywords: 4-bromophenol, thiomorpholine, IR

1

2

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 (C_sp2-H Ar), 2985 (C_sp3-H).

¹H-NMR (200 MHz; CDCl₃; Me₄Si, δ_H): 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; δ_C): 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%.

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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