Ethoxalyl chloride → 1-(5-Chloro-2-methylphenyl)-3-(2-propynyl)-2-thioxo-4,5-imidazolidinedione
反応式
Cl[C:2](=[O:8])[C:3]([O:5]CC)=O.[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([CH3:23])=[C:14]([NH:16][C:17]([NH:19][CH2:20][C:21]#[CH:22])=[S:18])[CH:15]=1>C(Cl)Cl>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([CH3:23])=[C:14]([N:16]2[C:2](=[O:8])[C:3](=[O:5])[N:19]([CH2:20][C:21]#[CH:22])[C:17]2=[S:18])[CH:15]=1参加物
4
実験手順
Ethyl chlorooxoacetate (11.2 mL; 0.1 mol) was added dropwise while cooling in an ice bath to the stirring solution of N-(5-chloro-2-methylphenyl)-N′-(2-propynyl)thiourea (11.95 g; 0.05 mol) in methylene chloride (200 mL). The mixture was stirred for 18 hours at ambient temperature then evaporated to dryness. The residue was stirred in ether (200 mL) and the solids were collected by filtration and air dried to give 3.0 g 1-(5-chloro-2-methylphenyl)-3-(2-propynyl)-2-thioxo-4,5-imidazolidinedione, m.p. 162–164° C. Mass spectrum; (El, M.+) m/z 292/294. 1H-NMR (DMSO-d6; 300 MHz): δ 7.50–7.47 (m, 2H), 7.73 (d, 1H), 4.66 (q, 2H), 3.37 (t, 1H), and 2.15 ppm (s,3H).