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Substitution reaction of 5,5-dimethylrhodanine with methylhydrazine and imination with benzaldehyde; 2-(benzylidenemethylhydrazino)-5,5-dimethyl-2-thiazolin-4-one

SyntheticPage 477
DOI: 10.1039/SP477
Submitted Jan 05, 2011, published May 17, 2011
John Davidson (jsdcrosslaw@tiscali.co.uk)
A contribution from Crosslaw
Reaction Scheme: <IMG src="/images/empty.gif">Substitution reaction of <SPAN id=csm1305874501890 class=csm-chemical-name title=5,5-dimethylrhodanine grpid="1">5,5-dimethylrhodanine</SPAN> with <SPAN id=csm1305874493337 class=csm-chemical-name title=methylhydrazine grpid="2">methylhydrazine</SPAN> and imination with <SPAN id=csm1305874510981 class=csm-chemical-name title=benzaldehyde grpid="4">benzaldehyde</SPAN><IMG src="/images/empty.gif">

Chemicals Used

5,5-dimethylrhodanine
methylhydrazine
methanol
benzaldehyde
ethanol

Procedure

5,5-dimethylrhodanine (1.3 g, 0.008mole) and methylhydrazine (0.8 ml, 0.015 mole) were stirred overnight in methanol (20ml). Next day, some sulphur which had separated was filtered off and benzaldehyde (1.6ml, 0.015 mole) was added to the filtrate.Next day the product (1.1 g, 52%) was filltered off and washed with a little ethanol.

Author's Comments

All manipulations were performed in a fume cupboard.

Data

Mp 170-171°(from ethanol) 
Found: C 59.99%, H 5.63%, N 16.12%.  C13H15N3OS requires C 59.74%, H 5.79%, N 16.08%
NMR and infrared spectra have been published by Sadtler. i.r. 79769K, n.m.r. 52712M in CDCl3

δ 1.69 (6H, s, Me2 ), δ 3.74(3H, s, Me), δ 7.72 (5H, Ar), δ 7.8 (1H, CH)

Lead Reference

J. S. Davidson, J. Chem. Soc.,1964,5903-5904

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Keywords: aldehydes, amines, condensation, heterocyclic compounds, imine, substitution