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CAS No. : | 6843-45-4 | MDL No. : | MFCD12755958 |
Formula : | C4H6N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 114.10 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trifluoroacetic acid for 1h; Heating; | ||
With sulfuric acid In water at 24.9℃; ΔH(excit); ΔS(excit). Various temperatures, reagents and pH; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 0℃; sowie bei 25grad; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | In toluene Heating; | |
68% | In toluene for 2h; Reflux; | 10149] Preparation of 3-methylimidazolidine-2,4-dione To a solution of hydantoin (0.50 g, 5.0 mmol) in toluene(30 mE), i, i -dimethoxy-N,N-dimethylethanamine (i .3 g, i 0 mmol, 2 equiv) was added. The mixture was refluxed for 2 hours then allowed to cool down to room temperature. Direct crystallization from the toluene gives 3-methylimi- dazolidine-2,4-dione (i) as a white solid (0.39 g, 68% yield) without thrther purification. ‘H NMR (400 MHz, CD3OD):ö8.Oi (s, iH), 3.88 (s, iH), 2.8i (s, iH). ‘3C NMR (400 MHz, CD3OD): öi72.9, i58.9, 46.0, 23.2. |
62% | In toluene for 3h; Heating; |
50% | In toluene at 110℃; for 2h; | 3 2,4-imidazolinedione (1.0 equiv) was dissolved in 40 ml of toluene,N, N-dimethylacetamide dimethyl acetal (N, N-dimethylacetamide dimethyl acetal) (3.0 equiv)The reaction solution was stirred at 110 ° C for 2 hours and then cooled to room temperature and cooled to 0 ° C for 15 minutes.Filter to get residue,The residue was washed five times with toluene and dried in vacuo to give 3-methylimidazolidine-2,4-dione (3-methyl-imidazoline-2,4-dione).Yield 50%. |
In toluene at 110℃; for 2h; | 1.16 Hydantoin (19.0 g, 190 mmol, 1.0 eq) was suspended in toluene (700 ml) and N,N-dimethylacetamide dimethyl acetal (75.0 g, 563 mmol, 3.0 eq) was added. The resulting mixture was heated at 110 °C for two hours, cooled to ambient temperature and then cooled to 0° C for 15 minutes. The resulting precipitate was collected by filtration, washed with toluene (5 x 50 mL) and dried in vacuo to afford the titled compound as a pale yellow solid. NMR (400 MHz, CDC13) δ 6.09 (1 H, brs); 3.99 (1 H, s); 3.04 (1 H, s) ppm. | |
In toluene for 3h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With piperidine; at 110℃; for 4h; | We heated a mixture of (1-6) (1 mmol) and l-methylimidazol-255(l,3H)- dione (which we synthesized according to the method used by Janin et al., Eur. <n="126"/>J. Org. Chem. 2002:1763-1769, 2002) (250mg, 2.5 mmol) in piperidine (2 mL) at 1100C for four hours under an argon atmosphere. Then, we allowed the reaction mixture to cool in a refrigerator (~ 5C) with the addition of ether (2 mL). We filtered the precipitate and washed it with ether to give (1-7). 1H NMR (500 MHz, DMSO-d6): delta 12.15 (IH, br s), 10.26 (IH, br s), 8.23 (IH, s), 7.79 (IH, d, J = 8.0 Hz), 7.27 (IH, d, J = 8.0 Hz,), 7.13 (IH, t, J = 7.8 Hz), 6.82 (IH, s), 2.97 (3H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With piperidine at 110℃; for 6h; Sealed tube; | Preparation of 5-((7-bromo- iH-indol-3-yl)methyl-ene)-3-methylimidazolidine-2,4-dione (2). To a solution of 7-bromo-i H-indole-3-carbaldehyde (220 mg, i.0 mmol) in piperidine (2 mE) in a seal tube was added 3-methylimida- zolidine-2,4-dione (i) (230 mg, 2.0 mmol, 2 equiv). Thetube was sealed and the reaction mixture was heated for 6 hours at 1100 C. Afier cooling down to room temperature, the mixture was transferred to water (100 mL) using a pipet. The target compound was filtered out as yellow precipitate (234 mg, 73% yield) without further purification. ‘H NMR (300 MHz, DMSO-d6): ö 8.19 (s, 1H), 7.80 (dd, J=8.02, 0.80 Hz, 1H), 7.38 (dd, J=7.59, 0.74 Hz, 1H), 7.04 (t, J=7.78 Hz, 1H), 6.77 (d, J=0.53 Hz, 1H), 2.93 (s, 3H). |
With piperidine In ethanol at 90℃; for 16h; |