2-(2-Imino-1-methylimidazolidin-4-ylidene)hydrazinecarbothioamide

Ahmed A. Al-Amiery; Abdul Amir H. Kadhum; Abu Bakar Mohamad

doi:10.3390/M763

,

and

¹

Chemical Engineering Faculty, University of Kabengassan Malaysia (UKM), Selangor, 43000, Malaysia

²

Applied Chemistry division, Applied Science Department, University of Technology (UOT), Baghdad, Iraq

^*

Author to whom correspondence should be addressed.

Molbank2012, 2012(3), M763;https://doi.org/10.3390/M763

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Abstract

A new thiosemicarbazone, 1-methyl-2-imino-N-(methanethialdiamine)-yl-4-iminoimidazolidin was synthesized and its UV-VIS, IR, and NMR spectroscopic data and CHN analysis are presented.

Keywords:

2-(2-imino-1-methylimidazolidin-4-ylidene)hydrazinecarbothioamide; thiosemicarbazide; thiosemicarbazones

The chemistry of thiosemicarbazones has received considerable attention because of their variable bonding modes, promising biological implications, structural diversity, and ion-sensing ability [1,2]. They have been used as drugs and are reported to possess a wide variety of biological activities against bacteria, fungi, and certain type of tumors, and they are also a useful model for bioinorganic processes [3]. In continuation of previous studies [4,5,6,7,8,9,10,11,12,13,14], we have focused on synthesis of new heterocyclic compounds, and herein we are reporting the synthesis of 1-methyl-2-imino-N-(methanethialdiamine)-yl-4-iminoimidazolidin as new molecule (Scheme 1).

Scheme 1. Synthesis of 1-methyl-2-imino-N-(methanethialdiamine)-yl-4-iminoimidazolidin.

Experimental

Synthesis of 2-(2-Imino-1-methylimidazolidin-4-ylidene)hydrazinecarbothioamide

A mixture of 1-methyl-4-oxo-2-iminoimidazolidin (2.26 g, 0.02 mol) and thiosemicarbazide (1.82 g, 0.02 mol) in 100 mL of ethanol was refluxed for 3 h. The solvent was evaporated on a rotary evaporator. The title compound was washed with cold ethanol, and dried under vacuum over P₄O₁₀. Yield 70%, (light brown) [7].

Melting point: 153 °C.

UV-VIS in DMF 255 and 322 nm.

FT-IR spectroscopy; 3421 cm⁻¹ (N-H stretching vibrations, NH₂); 1631 cm⁻¹ (C=N) and 1618 cm⁻¹ (C=N).

¹H-NMR (300 MHz, DMSO-d₆): 1.80 (s, 1H, NH), 2.20 (s, 3H, CH₃), 2.70 (s, 2H, CH₂), 8.00 (s, 1H, NH), 9.10 (s, 1H, NH) and 10.90 (s, 1H, NH).

Elemental analysis: C, 32.25 (31.91); H, 5.41 (5.11); N, 45.13 (44.74).

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgements

This study was supported by University of Technology, Baghdad, Iraq and Universiti Kebangsaan Malaysia under the DIP-2012-02 grant.

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