Ethoxalyl chloride → 3-[4,5-Dioxo-2-thioxo-3-(1,2,2-trimethyl-propyl)-imidazolidin-1-yl]-benzonitrile
Reaktionsgleichung
Cl[C:2](=[O:8])[C:3]([O:5]CC)=O.[C:9]([C:11]1[CH:12]=[C:13]([NH:17][C:18]([NH:20][CH:21]([CH3:26])[C:22]([CH3:25])([CH3:24])[CH3:23])=[S:19])[CH:14]=[CH:15][CH:16]=1)#[N:10]>ClCCl>[O:8]=[C:2]1[C:3](=[O:5])[N:17]([C:13]2[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=2)[C:9]#[N:10])[C:18](=[S:19])[N:20]1[CH:21]([CH3:26])[C:22]([CH3:25])([CH3:24])[CH3:23]Komponenten
4
Versuchsvorschrift
Ethyl chlorooxoacetate (1.03 mL, 9.17 mmol) was added to a stirring solution of the above thiourea (1.19 g, 4.59 mmol) in dichloromethane (30 mL) and the resulting mixture was stirred overnight at room temperature. Concentration, trituration of the residue with diethyl ether, and filtration afforded 1.167 g (81%) of 3-[4,5-dioxo-2-thioxo-3-(1,2,2-trimethyl-propyl)-imidazolidin-1-yl]-benzonitrile as a yellow solid: mp 168.1–168.7° C.; 1H NMR (DMSO-d6): δ8.00 (d, 1H), 7.84 (s, 1H), 7.75 (m, 2H), 4.83 (q, 1H), 1.47 (d, 3H), 1.01 (s, 9H); IR (KBr): 3500, 2970, 2230, 1765, 1600 cm−1; MS (m/z) 315 (M+).