Hydrazinolysis of 5,5-dialkyl-4-oxazolidinone-2-thiones; 2-(benzylidenemethylhydrazino)-5,5-dimethyl-2-oxazolin-4-one
SyntheticPage 467
DOI:
10.1039/SP467
Submitted Sep 27, 2010, published Sep 30, 2010
John Davidson (
jsdcrosslaw@tiscali.co.uk)
A contribution from
Crosslaw
Chemicals Used
5,5-dimethyl-4-oxazolidinone-2-thione
methylhydrazine
methanol
benzaldehyde
ethanol
Procedure
Methylhydrazine (1.02 ml) was added to a solution of 5,5-dimethyl-4-oxazolidinone-2-thione (2.9 g) in methanol (15 ml). After 4 h, benzaldehyde (2.2 ml) was added. On seeding, the product separated. Next day, the solid was filtered off, washed with a little ethanol to afford 3.48 g (71%),
Author's Comments
Prepared in fume cupboard.
Similarly but using benzylhydrazine gave 2-(benzylidenebenzylhydrazino)-5,5-dimethyl-2-oxazolin-4-one (32%),
mp 190-191°C was obtained.
Data
mp 187-188 ºC. Recryst. ethanol, mp 188-189 ºC.
Found: C 63.39%, H 5.95%, N 17.03%. C13H15N3O2 requires, C 63.66%, H 6.16%, N 17.13%
NMR (in CDCl3) d 1.58 s (6H), Me2, δ 3.63 s (3H) Me, δ 7.2-8.0 m (5H) Ph, δ 7.9 (1H) CH.
Lead Reference
Davidson, J. S. (1974), Hydrazinolysis of 5,5-Dialkyl-4-oxazolidinone-2-thiones. Journal für Praktische Chemie, 316: 1037–1040. DOI: 10.1002/prac.19743160621
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Get structure file (.cdx, .sk2, .mol)
Keywords: aldehydes, condensation, dialkyl-4-oxazolidinone-2-thiones, heterocyclic compounds, nucleophilic
