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2-[(2-Isopropyl-5-methylphenoxy)acetyl]-N-phenylhydrazine Carbothioamide
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Molbank 2002, 2002(1), M280; https://doi.org/10.3390/M280

Short Note
5-[(2-Isopropyl-5-methylphenoxy)methyl]-4-phenyl-4H-1,2,4-triazole-3-thiol
Chemistry Department, Faculty of Science, King Abdul-Aziz University, Jeddah 21589, P.O. Box 80203, Saudi Arabia
Tel.(+966)-2-6952293 Fax (+966)-2-6952293,
Received: 16 January 2002; in revised form: 15 March 2002 / Accepted: 15 May 2002 / Published: 16 February 2003
Keywords:
triazole; thymol; thiol; phenylhydrazine carbothioamide
Molbank 2002 m280 i001
The triazole derivative 2 was prepared from 2-[(2-isopropyl-5-methylphenoxy)acetyl]-N-phenylhydrazine carbothioamide (1) by heating under reflux with aqueous NaOH [1,2]. 1 (1.0 g, 2.80 mmol) was suspended in aqueous NaOH (15 ml, 8%) and heated under reflux for 5 hours. The reaction mixture was treated with charcoal and filtered. The filtrate was cooled to room temperature and acidified carefully with dilute acetic acid (10%). The precipitate thus formed was filtered, washed with copious amount of water and recrystallized from ethanol to give 2 as white crystals (0.81 g, 85%).
M.p. 165-167 oC (EtOH, uncorrected).
UV λmax (nm; Acetone)/e (dm3.mol-1.cm-1) 336/2900.
IR νmax (cm-1; KBr Disk) 3450 (NH), 2657 (SH), 1612 (C=N), 1581 (NH bending).
1H-NMR (400 MHz; CDCl3; Me4Si δH) 1.08 (6H, d, 2CH3), 2.27 (3H, s CH3), 2.98 (1H, m, CH), 4.90 (2H, S, CH2O), 6.57 (1H, s), 6.78 1H, d, J = 7.67 Hz), 7.07 (1H, d, J =7.70 Hz), 7.46 (1H, s, SH), 7.53 (3H, m), 7.54 (2H, m) .
13C-NMR (δC) 21.65, 23.43, 26.2, 60.74, (CH2O), 113.15, 123.2, 126.7, 128.2, 130.14, 130.6, 133.4, 134.96, 136.9, 149.08, 154.62, 169.78 (C-SH).
Elemental Analysis: Calculated for C19H21N3OS ( 339.22): C 67.27, H 6.19, N 12.39; found : C 67.12, H 5.96 , N 12.13.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

References

  1. Trivedi, S.; Kubavate, H.; Parekh, H. Indian J. Chem. 1994, 33, 295.
  2. Vashi, S.; Mehta, S.; Shah, V. H. Indian J. Chem. 1996, 35, 11.
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