Molbank 2005, M399

http://www.mdpi.net/molbank/

 

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

 

A. Ma. Vel¨¢zquez1, L.Torres1, R.Gonz¨¢lez1, A.Valencia1, I.Mart¨ªnez1, A.Pecina1, 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 del Estado de Hidalgo

 

e-mail: [email protected]

 

Received: 2 April 2004 / Accepted: 31 May 2004 / Published: 1 July 2005

 

Keywords: phenol, thiomorpholine

 

 

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¡ã (ethanol, uncorrected)

 

IR (CHCl3 film, cm-1): 3429 (O-H); 3065 (Csp2-H Ar); 2872 (Csp3-H).

 

1H-NMR (300 MHz; CDCl3): ¦Ä= 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): ¦Ä= 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%.

 

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. Artico, M.; Mai, A.; Sbardella, G.; Massa, S.; Lampis, G.; Deidda, D.; Pompei, R. Bioorganic & Medicinal Chemistry Letters  1998,  8,  1493-1498.

2. Biava, M.; Fioravanti, R.; Porretta, G.C.; Deidda, D.; Maullu, C.; Pompei, R. Bioorganic & Medicinal Chemistry Letters  1999,  9,  2983-2988.

3. Mai, A.; Sbardella, G.; Artico, M.; Massa, S.; Lampis, G.; Deidda, D.; Pompei, R. Medicinal Chemistry Research  1999,  9,  149-161.

 

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