Abstract
New kind of 5-aryl-2-thioxoimidazolidin-4-ones synthesis by condensation of arylglyoxal hydrates with thiourea in acetic acid solution at room temperatures has been developed.
Highlights
In this work 5-phenyl-2-thiohydantoin (1a) structure of the condensation product no had been established by the author, only it has relevant of the data of the elemental analysis
A mixture of 4-nitrophenylglyoxal hydrate (146 mg, 1.463 mmol), thiourea (71 mg, 0.928 mmol) and AcOH (6 mL) was stirred at 15°С for 10 min, maintained 18-19°С for 161 h, the solvent was evaporated under vacuum 4 Torr at 25-30°С, the residue was washed by cold water (8 ml), dried under vacuum 4 Torr at 16°С, yielding (163 mg, 92%) 5(4’-nitrophenyl)-2-thioxoimidazolidin-4-one (1e), yellow crystals, m.decomp. 245 – 246°С (THF – PhH – C6H14).1H NMR spectrum, 400 MHz, (CD3)2SO, δ, ppm, (J, Hz): δ = 5.66 (1H, s, CH); 7.58 (2H, d, 3J = 8.4, H2,6C6H4); 8.30 (2H, d, 3J = 8.4 H3,5C6H4); 10.64 (1H, s, NH); 12.03 (1H, s, NHC(O))
A mixture of 4-methylphenylglyoxal hydrate (256 mg, 1.542 mmol), thiourea (147 mg, 1.928 mmol) and AcOH (14 mL) was stirred at 15°С for 15 min, maintained 20°С for 65 h, the solvent was evaporated under vacuum 4 Torr at 25-30°С, the residue was washed by cold water (11 ml), dried under vacuum 4 Torr at 15°С, yielding (310 mg, 97%) 5-(4’-methylphenyl)-2-thioxoimidazolidin-4-one 1f, white crystals, m.p. 226 – 228°С.1H NMR spectrum, 400 MHz, (CD3)2SO, δ, ppm, (J, Hz): δ = 2.31 (3H, s, Me); 5.33 (1H, s, CH); 7.15 (2H, d, 3J = 8.0, H2,6C6H4); 7.23 (2H, d, 3J = 8.0, H3,5C6H4); 10.43 (1H, s, NH); 11.80 (1H, s, NHC(O))
Summary
5-phenyl-2-thioxoimidazolidin-4-one (1a) had been synthesized from phenylglyoxal hydrate by interaction with thiourea in aqueous solution at room temperatures.1 But in this work 5-phenyl-2-thiohydantoin (1a) structure of the condensation product no had been established by the author, only it has relevant of the data of the elemental analysis.1 Only recently the strictly evidence that phenylglyoxal hydrate interaction with thiourea acetic acid solution at 100oC yielded 1a had been done2 (Scheme 1).
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