Category: 496-46-8

A common heterocyclic compound, 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, molecular formula is C4H6N4O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 496-46-8.

3a-Methylglycoluril 1 (0.26 g, 1.67 mmol), glycoluril 2 (1.42 g, 10 mmol) and paraformaldehyde (0.9 g, 30 mmol) were added to concentrated hydrochloric acid (5 ml), and the resultant mixture was heated at 95 C for 24 h. After evaporation of the solvent, the residue was added to water (300 ml) and heated under stirring. The white solid was filtered, and then added to a mixed solvent (30 ml) consisting of formic acid and acetic acid in a ratio of 2:1 (v/v). After thorough stirring, the insoluble material (CB[6]) was removed by filtration, and acetone was added to the acidic filtrate. The precipitates generated therein were collected to afford the desired product 4 in a yield of 14%. TOF mass: m/z 1033 (M+Na+). 1H NMR (500 MHz, in D2O with Na2SO4): delta 5.66 (d, Jin,out = 15.8 Hz, 11H, methylene Hout), 5.59 (d, Jin,out = 16 Hz, 1H, methylene Hout), 5.55 (s, 10H, methine H), 5.29 (s, 1H, methine H), 4.35 (d, Jin,out = 16 Hz, 1H, methylene Hin), 4.28 (d, Jin,out = 15.8 Hz, 11H, methylene Hin) and 1.75 ppm (s, 3H, methyl H). 13C NMR (125 MHz, in D2O with Na2SO4): delta 157.7 (C’O), 157.2 (CO), 77.1 (CH), 74.8 (C-CH3), 71.0 (CH), 52.1 (CH2), 48.1 (CH2) and 20.2 ppm (CH3).

The synthetic route of Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ahmed, Mostafa M.; Koga, Kazutaka; Fukudome, Makoto; Sasaki, Hideaki; Yuan, De-Qi; Tetrahedron Letters; vol. 52; 36; (2011); p. 4646 – 4649;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

496-46-8, Adding some certain compound to certain chemical reactions, such as: 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 496-46-8.

14.2 g (100 mmol) of glycoluril,16.0 g (400 mmol) of sodium hydroxide and 140 mL of dimethylsulfoxide were mixed,After heating and stirring at 40 C. for 1 hour, And 34.4 g (400 mmol) of allyl chloride were added dropwise at the same temperature over 20 minutes, and the mixture was heated and stirred at 40 C. for 2 hours to complete the reaction.The resulting reaction mixture was evaporated to dryness under reduced pressure, and the obtained dry solid was separated and extracted with 400 mL of ethyl acetate and 400 mL of water, and the ethyl acetate layer was washed with 100 mL of water, then with 100 mL of saturated brine, Dried over sodium sulfate, and ethyl acetate was distilled off under reduced pressure to obtain 27.4 g of 1,3,4,6-tetraallyl glycoluril as a colorless oil, yield 90%.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 496-46-8.

Reference:
Patent; Shikoku Chemicals Co., Ltd.; Takeda, Takuma; Kashihara, Takashi; Kumano, Noboru; Mizobe, Noboru; (59 pag.)JP2015/59101; (2015); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

496-46-8, Name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, 496-46-8, 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.

Synthesis of cucurbit[n]urils in methanesulphonic acid usingDipropoxymethane (Propylal)Unsubstituted glycoluril (19.94 g) and methane sulphonic acid (neat, 82 mL) were placed in a reaction flask and heated to 80 C. Propylal (45 mL) was added in drop-wise and the reaction mixture was then heated to 100 C (internal temp) for 18 hours. The reaction mixture was cooled and added to acetone (410 ml) to produce a beige powder which was analysed by1H NMR. Approximate Yields by1H NMR (% of recovered product) cucurbit[5]urii 0%, cucurbit[8]uril 58%, cucurbit[7]uril 42%, cucurbit[8]uril 0%, cucurbit[9]uril 0%, cucurbit[10]uril 0%, cucurbit[11]urii 0%. Residual formaldehyde by HPLC method was 5 ppm.

Statistics shows that Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione is playing an increasingly important role. we look forward to future research findings about 496-46-8.

Reference:
Patent; AQDOT LIMITED; COULSTON, Roger; DIEC, David; NOGUEIRA, Guilherme; GERARDUS DE ROOIJ, Johannes; (23 pag.)WO2018/115822; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem