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Short 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
Submission received: 2 April 2004 / Accepted: 31 May 2004 / Published: 1 July 2005
Versions Notes

Keywords:
phenol; thiomorpholine

Molbank 2005 m399 i001
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 materials

Supplementary File 1Supplementary File 2Supplementary File 3

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.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. Artico, M.; Mai, A.; Sbardella, G.; Massa, S.; Lampis, G.; Deidda, D.; Pompei, R. Bioorganic & Medicinal Chemistry Letters 1999, 8, 1493–1498.
  2. Biava, M.; Fioravanti, R.; Porretta, G.C.; Deidda, D.; Maullu, C.; Pompei, R. Bioorganic & Medicinal Chemistry Letters 1999, 9, 2083–2988.
  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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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.; et al. 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, et al. 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, and et al. 2005. "Synthesis of 4,6-bis(thiomorpholin-4-ylmethyl)-1,2,3-benzenetriol" Molbank 2005, no. 1: M399. https://doi.org/10.3390/M399

APA 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. (2005). Synthesis of 4,6-bis(thiomorpholin-4-ylmethyl)-1,2,3-benzenetriol. Molbank, 2005(1), M399. https://doi.org/10.3390/M399

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