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Volume 2005
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Short Note

Synthesis of 4-chloro-2-(thiomorpholin-4-ylmethyl)phenol

by
A. Ma. Velázquez
1,
L. Torres
1,
R. González
1,
A. Valencia
1,
A. Pecina
1,
I. Menconi
1,
I. Martínez
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), M400; https://doi.org/10.3390/M400
Submission received: 2 April 2004 / Accepted: 31 May 2004 / Published: 1 July 2005
Versions Notes

Keywords:
phenol; thiomorpholine

Molbank 2005 m400 i001
4-chloro-2-(thiomorpholin-4-ylmethyl)phenol (2) was prepared from 4-chlorophenol (1) and thiomorpholine and formaldehyde (37%) in methanol as solvent . A solution of methanol (50 mL) and 4-chlorophenol 1 (1.26g, 9.80 mmol) was prepared and heated at 40 °C for 15 minutes, after that a solution of thiomorfoline (2.0g, 20.7 mmol) and formaldehyde (1.5 mL, 20.15 mmol) in methanol was added . When the addition was completed, the reaction mixture was stirred at reflux for 24 hrs. The solvent was eliminated using rotavapor and reaction mixture was poured into water and extracted with ehtyl acetate. The product was crystallized after eliminated solvent and recrystallized from ethanol as white powder (2) (25% yield).
Melting Point: 127-129 °C (methanol, uncorrected).
IR (CHCl3 film, cm-1): 3502 (O-H); 3010 (Csp2-H Ar); 2985 (Csp3-H).
1H-NMR (300 MHz; CDCl3): δ= 10.56 (1H, s, OH); 7.11 (1H, dd, J= 8.7Hz, 2.7Hz); 6.94 (1H, d, J= 2.7Hz); 6.74 (1H, d, 8.7Hz); 3.65 (2H, s, Ar-CH2); 2.81 (4H, m, -S-CH2-); 2.71 (4H, m, -N-CH2-).
13C-NMR (75 MHz; CDCl3): δ= 156 (C); 128.56 (CH); 128.31 (CH); 123.61 (C); 122.11(C); 117.37 (CH); 61.63 (Ar-CH2); 54.27 (-S-CH2-); 27.73 (-N-CH2-).
MS (FAB; m/z, %): 244(100%); 215; 180; 154.
Elemental Analysis: Calculated for C11H14NOSCl: C, 54.20%; H, 5.79%; N, 5.75%; O, 6.56%; S, 13.15%; Cl, 14.54%. Found: C, 54.40%; H, 5.77%; N, 5.80%; O, 6.45%; S, 13.22%; Cl, 14.49%.

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. Biava, M.; Fioravanti, R.; Porretta, G.C.; Deidda, D.; Maullu, C.; Pompei, M. Biorg.& Med.Chem.Lett. 1999, 9, 2083–2985.
  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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MDPI and ACS Style

Velázquez, A.M.; Torres, L.; González, R.; Valencia, A.; Pecina, A.; Menconi, I.; Martínez, I.; Martínez, L.; Ramírez, A.; Hernández, R.; et al. Synthesis of 4-chloro-2-(thiomorpholin-4-ylmethyl)phenol. Molbank 2005, 2005, M400. https://doi.org/10.3390/M400

AMA Style

Velázquez AM, Torres L, González R, Valencia A, Pecina A, Menconi I, Martínez I, Martínez L, Ramírez A, Hernández R, et al. Synthesis of 4-chloro-2-(thiomorpholin-4-ylmethyl)phenol. Molbank. 2005; 2005(1):M400. https://doi.org/10.3390/M400

Chicago/Turabian Style

Velázquez, A. Ma., L. Torres, R. González, A. Valencia, A. Pecina, I. Menconi, I. Martínez, L. Martínez, A. Ramírez, R. Hernández, and et al. 2005. "Synthesis of 4-chloro-2-(thiomorpholin-4-ylmethyl)phenol" Molbank 2005, no. 1: M400. https://doi.org/10.3390/M400

APA Style

Velázquez, A. M., Torres, L., González, R., Valencia, A., Pecina, A., Menconi, I., Martínez, I., Martínez, L., Ramírez, A., Hernández, R., López-Castañares, R., Olvera-Neria, O., & Angeles, E. (2005). Synthesis of 4-chloro-2-(thiomorpholin-4-ylmethyl)phenol. Molbank, 2005(1), M400. https://doi.org/10.3390/M400

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