Molbank 2005, M401 |
A. Ma. Vel¨¢zquez1, L.Torres1,
R.Gonz¨¢lez1, I.Mart¨ªnez1, A.Valencia1,
A.Pecina1, L.Torres, I.Menconi1,
L.Mart¨ªnez1, A.Ram¨ªrez1, R.Hern¨¢ndez1,
R.L¨®pez-Castañares2 , O.Olvera-Neria3, E.Angeles*1,
1) Facultad de Estudios Superiores Cuautitl¨¢n, Universidad Nacional Aut¨®noma de M¨¦xico,
2) Facultad de Qu¨ªmica de la UAEM,
3) Instituto de Ciencias B¨¢sicas e Ingenieria, Universidad Aut¨®noma
e-mail: [email protected]
Received:
Keywords:
phenol, thiomorpholine
4-tert-butyl-2-(thiomorpholin-4-ylmethyl)phenol (2)
and 4-tert-butyl-2,6-bis(thiomorpholin-4-ylmethyl)phenol
(3) were prepared from 4-
tert-butylphenol (1)
and thiomorpholine and formaldehyde (37%) in methanol as solvent . A solution of
methanol (50 mL) and 4-tert-butylphenol
(
4-tert-butyl-2-(thiomorpholin-4-ylmethyl)phenol (2)
Melting Point: 85-87 C¡ã (methanol, uncorrected).
IR (CHCl3 film; cm-1): 3456 (O-H); 3197 (Csp2-H Ar); 2886 (Csp3-H).
1H-NMR (300 MHz; CDCl3): ¦Ä= 10.33 (1H, s, OH); 7.18 (1H, dd, J= 8.4Hz, 2.7Hz); 6.94 (1H, d, J= 2.7Hz); 6.74 (1H, d, 8.4Hz); 3.70 (2H, s, Ar-CH2); 2.82 (4H, m, -S-CH2-); 2.71 (4H, m, -N-CH2-); 1.27 (9H, CH3).
13C-NMR (75 MHz; CDCl3): ¦Ä= 155 (C); 141.8 (C); 125.60 (CH); 125.49 (CH); 119.77(C); 115.47 (CH); 62.51 (Ar-CH2); 54.36 (-N-CH2-); 33.84 (C); 31.48 (CH3); 27.79 (-S-CH2-).
MS (FAB; m/z, %): 266(80%); 265 (100%); 163(45%).
Elemental Analysis: Calculated for C15H23NOS:
C, 67.88%; H, 8.73%; N, 5.28%; O, 6.03%; S, 12.08%. Found: C, 67.58%; H, 8.75%;
N, 5.41%; O, 6.09%; S, 12.01%.
4-tert-butyl-2,6-bis(thiomorpholin-4-ylmethyl)phenol (3)
Melting
Point: 95-97 C¡ã (methanol,
uncorrected).
IR (CHCl3 film; cm-1): 3403 (O-H); 3089 (Csp2-H Ar); 2986 (Csp3-H).
1H-NMR (300 MHz; CDCl3): ¦Ä=10.69 (1H, s, OH); 7.09 (2H, s); 3.71 (4H, s, Ar-CH2); 2.86 (8H, m, -S-CH2-); 2.76 (8H, m, -N-CH2-); 1.27 (9H, CH3).
13C-NMR (75 MHz; CDCl3): ¦Ä=153.6 (C); 141.14 (C); 125.79 (CH); 121.22 (C); 58.81 (Ar-CH2); 54.42 (-N-CH2-); 33.78 (C); 31.47 (CH3); 27.74 (-S-CH2-).
MS (FAB; m/z, %): 381 (35%); 278 (100%); 175 (50%).
Elemental Analysis: Calculated for C20H32N2OS2: C, 63.11%; H, 8.47%; N, 7.36%; O, 4.20%; S, 16.85%. Found: C, 63.42%; H, 8.51%; N, 7.29%; O, 4.25%; S, 16.91%.
Acknowledgements
The 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.Garc¨ªa, D.Jim¨¦nez 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 C¨¢tedra Qu¨ªmica Medicinal of FESC-UNAM.
References
1. Biava, M., Fioravanti, R., Porretta, G.C., Deidda,
D., Maullu, C., Pompei M. Biorg.& Med.Chem.Lett. 1999, 9, 2983-2988.
2. Teipel, S.; Griesar, K.; Haase, W.; Krebs, B. Inorganic
Chemistry 1994, 33, 456-64.
3. Hodgkin, J.H., Aust .J. Chem., 1984,
37, 2371-2378.
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