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Desulphurisation of 5,5-pentamethylene-4-oxazolidinone-2-thione; 5,5-pentamethyleneoxazolidine-2,4-dione

SyntheticPage 478
DOI: 10.1039/SP478
Submitted Jan 05, 2011, published Mar 05, 2011
John Davidson (jsdcrosslaw@tiscali.co.uk)
A contribution from Crosslaw


			Reaction Scheme: Desulphurisation of <SPAN id=csm1299581573966 class=csm-chemical-name title=5,5-pentamethylene-4-oxazolidinone-2-thione grpid="1">5,5-pentamethylene-4-oxazolidinone-2-thione</SPAN>

Chemicals Used

5,5-pentamethylene-4-oxazolidinone-2-thione
carbon tetrachloride
bromine
sulphur dioxide
ether
sodium sulphate
heptane

Procedure

A mixture of 5,5-pentamethylene-4-oxazolidinone-2-thione (0.02 mole), water (20 ml) and CCl4 was warmed up and then bromine (2 ml) added.  After cooling, SO2 was passed through the mixture until the colour of bromine had disappeared.  The product was extracted with ether (200 ml), the extract washed with water (30 ml) and dried over sodium sulphate. Next day the ether and CCl4 was distilled off on a water bath and the residue recrystallized from heptane (300 ml ) to afford 3.13 g (92%)

Author's Comments

Data

mp 112-113°  Lit. mp 110-111°, 110-112°
Found: C 56.8%, H 6.6%, N 8.2%  Calc. for C8H11NO3  C 56.8%, H 6.5%, N 8.25%.


Lead Reference

J. S. Davidson, J. Prakt. Chem., 1974, 316, 1037-1040
doi:10.1002/prac.19743160621

Other References

H. Beyer and R. Sporl, Chem. Ber., 1966, 99, 2719-2724
doi:10.1002/cber.19660990902
M. A. Spielman, J. Am. Chem. Soc., 1944, 66, 1244-1245
doi:10.1021/ja01236a005

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Get structure file (.cdx, .sk2, .mol)

Keywords: Desulfurisation

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