496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. COA of Formula: C4H6N4O2
EXAMPLE 2; AFFINITYPURIFICATION OFDIMETHYLCYCLOPENTANO-CB; Dimethylcyclopentano-CB (Figure 4, Compound 3) was synthesized according to the procedures described by Day et al. (J. Org. Chem. 2001, 66, 8094) and Isobe et al. (ORG. Lett. 2002, 4, 1287), by heating at 90 C for 24 hours, a 5 : 1 mixture of glycoluril (Compound 2) and dimethylcyclopentano-glycoluril (Figure 4, Compound 3), and formaldehyde in the presence of concentrated sulfuric acid (Figure 4), so as to give the desired cucurbituril product in 30 % yield. The water-soluble fraction (740 mg) of the crude, heterogeneous mixture (1.3 gram) was dissolved in neutral water (50 ml) and passed through a column loaded with the protonated aminated resin prepared as described above, at a flow rate of 0.5 ml/minute (of the heterogeneous mixture in water). The column was then washed sequentially with water, methanol, CH2C12, and again with methanol. Removal of the solvent from the combined eluent afforded a solid residue (510 mg). This residue was used for collecting a second harvest of CB [6] using the same column, as is detailed hereinbelow. A sample of the resin was dried under reduce pressure overnight and was analyzed by FTIR. The obtained spectrum, presented in Figure 13, indicated that the resin is indeed loaded with the CB [6]. The resin-bound CB [6] was released from the column by elution with a 1: 2 mixture of TRIETHYLAMINE-DMF (100 ml) at a flow rate of 2 ml/minute. The column was thereafter washed with water (200 ml), and the combined eluent was concentrated under reduced pressure. Methanol was then added and the precipitate was collected and dried. The resultant white powder (195 mg) was analyzed BY H NMR and ESI- MS and the analyses are presented in Figures 14 and 15, respectively. As is shown in Figures 14 and 15, the resin-bound CB [6], obtained as a powder upon elution from the column, contained mainly a mixture of Compound 4 (Figure 4) and Compound 1 (Figure 2), with a small amount of di (dimethylcyclopentano) -CB [6]. Regeneration of the column was performed by washing it with 10 % (v/v) trifluoroacetic acid in CH2C12. The regenerated column was used again to harvest additional amounts of CB [6] from the CB-depleted remnants obtained in the first harvest (510 mg). That residue was dissolved in neutral water and loaded on the column as described above. Unloading the column with triethylamine-DMF yielded a second crop of pure CB [6] (165 mg). The performance of the column over multiple cycles of affinity chromatography was evaluated by loading and unloading a sample of purified CB [6] (150 mg) four times. The sample was trapped and released quantitatively in all eight operations with no apparent loss of the column capacity.
The synthetic route of 496-46-8 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; TECHNION RESEARCH & DEVELOPMENT FOUNDATION LTD.; WO2005/23816; (2005); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem