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

Synthesis of 4-tert-butyl-2-(thiomorpholin-4-ylmethyl)phenol, and 4-tert-butyl-2,6-bis(thiomorpholin-4-ylmethyl)phenol

by
A. Ma. Velázquez
1,
L. Torres
1,
R. Gonzále
1,
I. Martínez
1,
A. Valencia
1,
A. Pecin
1,
L. Torres
1,
I. Mencon
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
*
Author to whom correspondence should be addressed.
Molbank 2005, 2005(1), M401; https://doi.org/10.3390/M401
Submission received: 2 April 2004 / Accepted: 31 May 2004 / Published: 1 July 2005
Versions Notes

Keywords:
phenol; thiomorpholine

Molbank 2005 m401 i001
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 (1.49 g, 9.92 mmol) 1 was prepared and and heated at 40 °C for 15 minutes, after that a solution of thiomorpholine (2.0 g, 20.7mmol) and formaldehyde (1.50 mL, 20.15 mmol) in methanol were 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 ethyl acetate. Chromatography on silica gel (30/70 EtOAc/n-hexane) afforded two crystalline products 2 and 3 (5% and 35 % yield).

4-tert-butyl-2-(thiomorpholin-4-ylmethyl)phenol (2)

Melting Point: 85-87 C° (methanol, uncorrected).
IR (CHCl3 film; cm-1): 3456 (O-H); 3197 (Csp2-H Ar); 2886 (Csp3-H).
1H-NMR (300 MHz; CDCl3): δ= 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): δ= 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° (methanol, uncorrected).
IR (CHCl3 film; cm-1): 3403 (O-H); 3089 (Csp2-H Ar); 2986 (Csp3-H).
1H-NMR (300 MHz; CDCl3): δ=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): δ=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%.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3Supplementary File 4Supplementary File 5Supplementary File 6

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, 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.
  • Molbank 2005 m401 i002

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MDPI and ACS Style

Velázquez, A.M.; Torres, L.; Gonzále, R.; Martínez, I.; Valencia, A.; Pecin, A.; Torres, L.; Mencon, I.; Martínez, L.; Ramírez, A.; et al. Synthesis of 4-tert-butyl-2-(thiomorpholin-4-ylmethyl)phenol, and 4-tert-butyl-2,6-bis(thiomorpholin-4-ylmethyl)phenol. Molbank 2005, 2005, M401. https://doi.org/10.3390/M401

AMA Style

Velázquez AM, Torres L, Gonzále R, Martínez I, Valencia A, Pecin A, Torres L, Mencon I, Martínez L, Ramírez A, et al. Synthesis of 4-tert-butyl-2-(thiomorpholin-4-ylmethyl)phenol, and 4-tert-butyl-2,6-bis(thiomorpholin-4-ylmethyl)phenol. Molbank. 2005; 2005(1):M401. https://doi.org/10.3390/M401

Chicago/Turabian Style

Velázquez, A. Ma., L. Torres, R. Gonzále, I. Martínez, A. Valencia, A. Pecin, L. Torres, I. Mencon, L. Martínez, A. Ramírez, and et al. 2005. "Synthesis of 4-tert-butyl-2-(thiomorpholin-4-ylmethyl)phenol, and 4-tert-butyl-2,6-bis(thiomorpholin-4-ylmethyl)phenol" Molbank 2005, no. 1: M401. https://doi.org/10.3390/M401

APA Style

Velázquez, A. M., Torres, L., Gonzále, R., Martínez, I., Valencia, A., Pecin, A., Torres, L., Mencon, I., Martínez, L., Ramírez, A., Hernández, R., López-Castañares, R., Olvera-Neria, O., & Angeles, E. (2005). Synthesis of 4-tert-butyl-2-(thiomorpholin-4-ylmethyl)phenol, and 4-tert-butyl-2,6-bis(thiomorpholin-4-ylmethyl)phenol. Molbank, 2005(1), M401. https://doi.org/10.3390/M401

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