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Molecules 2001, 6, M214

2-Mercapto-5-(2'-isopropyl-5'-methylphenoxymethyl)-1,3,4-triazole

Abdullah Mohamed Asiri

Chemistry Department, Faculty of Science, King Abdul-Aziz University, Jeddah 21589, P.O. Box 80203, Saudi Arabia. Tel.(+696)-2-6952293, Fax (+696)-2-6952293, E-mail: [email protected]

Received: 18 December 2000 / Accepted: 15 May 2001 / Published: 25 May 2001

The triazole derivative 2 was prepared from 4-[2'-isopropyl-5'-methylphenoxyacyl]thiosemicarbazide 1 by heating under reflux with aqueous NaOH [1,2]. 4-[2'-Isopropyl-5'-methylphenoxyacyl]thiosemicarbazide 1 (1.0 g, 3.56 mmol) was suspended in aqueous NaOH (10 mL, 8%) and heated under reflux for 4 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 (0.76 g, 81%).

Mp. 170-172°C (EtOH, uncorrected).

UV l_max (nm; Acetone)/e (dm³.mol^-1.cm^-1): 331/4718.

IR (KBr): 3500 (NH), 2657 (SH), 1600 (C=N), 1575 (NH bending).

¹H-NMR (400 MHz; CDC_l3; Me₄Si): 1.20, 1.23 (6H, d, 2CH₃), 2.31 (3H, s CH₃), 3.34 (1H, m, CH), 4.67 (2H, S, CH₂O), 6.56 (1H, s), 6.81 1H, d, J = 7.67 Hz), 7.12 (1H, d, J =7.70 Hz), 7.26 (1H, s, SH).

¹³C-NMR (100 MHz; CDCl₃):21.27, 22.82, 26.6, 65.35 (CH₂O), 112.5, 122.77, 126.42, 134.57, 136.52, 154.58, 173.5(C-SH).

Anal.Calc. for C₁₃H₁₇N₃OS (263.364): C 59.29, H 6.51, N 15.96; found : C 59.38, H 6.43 , N16.15.

References

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

Sample availability: available from the authors and MDPI.