2-[(2-isopropyl-5-methylphenoxy)acetyl]-N-phenylhydrazine carbothioamide

Molbank 2002, M279

www.molbank.org

2-[(2-Isopropyl-5-methylphenoxy)acetyl]-N-phenylhydrazine Carbothioamide

Abdullah Mohamed Asiri

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, E-mail: [email protected]

Received: 16 January 2002 / Revised: 15 March 2002 / Accepted: 15 May 2002 / Published: 16 February 2003

Keywords: phenylhydrazine carbothioamide, thymol, 2-isopropyl-5-methylphenoxyacyl hydrazide

The phenylthiosemicarbazide derivative 3 was prepared from 2-isopropyl-5-methylphenoxyacyl hydrazide (1) and phenyl isothiocyanate (2) [1,2]. A mixture of 1 (0.5 g, 2.25 mmol) and 2 (0.30 g, 2.25 mmol) in aqueous hydrochloric acid (15 mL, 50%) was heated under reflux for 3 hours. The reaction mixture was cooled to room temperature and the precipitate thus formed was filtered, washed with copious amount of water and recristallized from ethanol to give 3 as white cristals. (0.71 g, 88%).

M.p. 156-158 ^oC (EtOH, uncorrected).

UV lmax (nm; Acetone)/e (dm³.mol^-1.cm^-1) 274/17090, 355/4200.

IR nmax (cm^-1; KBr Disk) 3292, 3234 (NH), 2657 (SH), 1674 (C=O), 1553 (NH bending).

¹H-NMR (400 MHz; CDCl₃; Me₄Si) d_H 0.95 (6H, d, 2CH₃), 2.03 (3H, s CH₃), 3.17 (1H, m, CH), 4.36 (2H, S, CH₂O), 6.40 (1H, s), 6.51 1H, d, J = 7.63 Hz), 6.83 (1H, d, J =7.73 Hz), 6.88 (1H, d, J =7.35 Hz), 7.05 (2H, t, J =7.85 Hz), 7.24 (2H, d, J =7.5 Hz).

¹³C-NMR (d_C) 21.44, 23.24, 26.50, 67.15 (CH₂O), 112.5, 122.63, 124.0, 125.47, 126.3, 128.8,134.38, 136.7, 138.8154.58.

Elemental Analysis: Calculated for C₁₉H₂₃N₃O₂S ( 357.22): C 63.88, H 6.44, N 11.77; found : C 63.67, H 6.56 , N 11.62.

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.