Crystal structure of 3-benzyl-5,5-dimethylimidazolidine-2,4-dione, C₁₂H₁₄N₂O₂

Abstract

C 12 H 14 N 2 O 2 ,monoclinic, P12 1 /n1(no. 14), a =13.0062(3) Å, b =6.0105(1) Å, c =15.6960(4) Å, b =108.359(1)°, V =1164.6 Å 3 , Z =4,R gt (F) =0.043, Source of materialThe title compound has been obtained by regioselective N3-alkylation reaction of 5,5-dimethylimidazolidine-2,4-dione with benzyl bromide (1 equiv.) in dry N,N-dimethylformamide in the presence of potassium carbonate as ab ase [1,2]. The heterogeneous solution was heated at 85°Cfor six hours and concentrated in vacuo. The residue was diluted with water and the mixture extracted with dichloromethane. The combined organic extracts were dried with sodium sulfate and evaporated to give the title compound as ac olourless oil. Colourless needle-like crystals, suitable for X-ray structure analysis were obtained after slow evaporation of the solvent (dichloromethane/petroleum ether, 1:5, v/v)overnight at 273 Kand crystallization over aperiod of several days at 268 K(mp. 381 -383 K). DiscussionThe crystal structure contains 4symmetry-equivalent molecules per unit cell. All intramolecular bond lengths are normal. The main part of the molecule consists of an almost planar aromatic system (N1, C2, N3, C4, C5, O8, O9, C10) with an r.m.s. value of the deviations from the least squares plane of 0.018 Å.Asecond plane, which is defined by C10, C11, C12, C13, C14, C15, C16 with r.m.s. =0.009 Å,istilted by 85.83(3)°against the first. A third plane, defined by C5, C6 and C7, is tilted against the second one by 89.03 (8)

Regioselective synthesis of 7,8-dihydroimidazo[5,1-c][1,2,4]triazine-3,6(2H,4H)-dione derivatives: A new drug-like heterocyclic scaffold

“…Compounds 7 – 11 were isolated after chromatographic purification in good to excellent yields and analyzed by NMR spectroscopy ( 1 H and 13 C) and LC/ESI-MS. In addition, we obtained an X-ray crystal structure of 11 [18], which confirmed the alkylation at the N3-position of 5,5-dimethylhydantoin ( 6 ). The subsequent N1-alkylation of 2,5-dioxoimidazolidines 7 – 10 to the corresponding N , N -disubstituted hydantoins 12 – 18 was performed with 1.0–1.2 equiv of the appropriate alkylating reagent by using sodium hydride as a base in dry dimethylformamide (DMF) (Table 2).…”

“…N3- and subsequent N1-alkylation led to the N1,N3-dialkylated hydantoin derivatives 12 – 18 . Alkylation reactions of hydantoins are well documented in the literature [14–18]. Depending on the alkylation reagents and reaction conditions, either N1- or N3-substituted hydantoins are accessible [14–17].…”

“…Alkylation of the thermodynamically preferred N3-position was achieved following a modified literature procedure, and the products could be obtained on a multigram scale [18]. In general, 1.1 equivalents of the corresponding alkylation reagent and potassium carbonate as a base in dry dimethylformamide (DMF) were used.…”