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CAS No. : | 67337-74-0 | MDL No. : | MFCD01076167 |
Formula : | C4H6N2O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 130.10 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* 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 water; silver(l) oxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; potassium cyanate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With D-hydantoinase 1 In water at 50℃; for 16.6h; pH 8.5; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Serin, KOCN; | ||
Among the compounds of formula (II), mention may be made especially of the following preferred compounds: parabanic acid ... 5,5-dimethylhydantoin 5-n-propylhydantoin 5-ethyl-5-methylhydantoin 5-hydroxy-5-methylhydantoin 5-hydroxymethylhydantoin 1-allylhydantoin 1-aminohydantoin hydantoin 5-acetic acid ... | ||
Among the compounds of formula (II) mention made be made especially of the following particularly preferred compounds: 1,2-dihdryo-3-H-1,2,4-traizol-2-one ... 1,3-bis(2-hydroxyethyl)-2-imidazolidinone 2-imidazolidone-4-carboxylic acid 1-(2-aminoethyl)-2-imidazole hydantoin 5-hydroxymethylhydantoin hydantoin 5-acetic acid urazole orotic acid ... |
Among the compounds of formula (II) mention made be made especially of the following particularly preferred compounds: 1,2-dihdryo-3-H-1,2,4-traizol-2-one...1,3-bis(2-hydroxyethyl)-2-imidazolidinone2-imidazolidone-4-carboxylic acid1-(2-aminoethyl)-2-imidazolehydantoin5-hydroxymethylhydantoinhydantoin 5-acetic acidurazoleorotic acid... | ||
Among the compounds of formula (II), mention may be made especially of the following preferred compounds: parabanic acid...5,5-dimethylhydantoin5-n-propylhydantoin5-ethyl-5-methylhydantoin5-hydroxy-5-methylhydantoin5-hydroxymethylhydantoin1-allylhydantoin1-aminohydantoinhydantoin 5-acetic acid... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With dmap In N,N-dimethyl-formamide at 20℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide at 45℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With hydrogenchloride In water for 3h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5.1 g | With hydrogenchloride In water for 24h; Reflux; | 4.9. Synthesis of 5-hydroxymethylhydantoin (15) A solution of potassium cyanate (4.0 g, 49.4 mmol) and serine (4.0 g, 38.1 mmol) in water (50 ml) was heated under reflux for 90 min. After cooling at rt, hydrochloric acid (15 ml, 35% aq solution) was added and the mixture was heated under reflux for 24 h. The solvent was removed under reduced pressure, and the resulting solid was washed with methanol and dried, leading to 5-hydroxymethylhydantoin (5.1 g, 99% yield) as a white solid. Elemental analysis (C4H6N2O3): theoretical C 36.93, H 4.65, N 21.53; experimental: C 37.05, H 4.52, N 21.41. 1H NMR (DMSO-d6, δ ppm): 10.51 (s, 1H), 7.77 (s, 1H), 5.06 (m, 1H), 3.98 (m, 1H), 3.57 (m, 1H). 13C NMR (DMSO-d6, δ ppm): 109.0, 164.2, 66.7, 66.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine at 0 - 20℃; | 1 O4-[(2,5-Dioxoimidazolidin-4-yl)methyl]O1-methyl (E)-but-2-enedioate (1) 5-(Hydroxymethyl)imidazolidine-2,4-dione (1.5 eq) was added to a mixture of methyl hydrogen fumarate (MHF) (1.0 g, 1.0 eq), EDAC (or HBTU) (2.0 eq) and triethylamine (2.0 eq) in dichloromethane (or DMF) (20 mL). The mixture was stirred at 0° C. for 1 h and then at 20° C. overnight. The reaction was concentrated in vacuo to a residue and then purified by reverse-phase (C-18) liquid chromatography using water and acetonitrile as eluents to yield compound (1). MS (ESI): m/z 243.1 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine at 0 - 20℃; | 8 Bis[(2,5-dioxoimidazolidin-4-yl)methyl](E)-but-2-enedioate (8) 5-(Hydroxymethyl)imidazolidine-2,4-dione (2.5 eq) was added to a mixture of fumaric acid (FA) (1.0 g, 1.0 eq), EDAC (or HBTU) (4.0 eq) and triethylamine (6.0 eq) in dichloromethane (or DMF) (50 mL). The mixture was stirred at 0° C. for 1 h and then at 20° C. overnight. The reaction was concentrated in vacuo to a residue and then purified by reverse-phase (C-18) liquid chromatography using water and acetonitrile as eluents to yield compound (8). MS (ESI): m/z 341.1 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine at 0 - 20℃; | 6 01 -[(2,5-Dioxoimidazolidin-4-yl)methyl]04-(2-methylpropanoyloxymethyl) (E)-but-2-enedioate (6) 5-(Hydroxymethyl)imidazolidine-2,4-dione (1.5 eq) was added to a mixture of compound (6b) (0.10 g, 1.0 eq), EDAC (or HI3TU) (2.0 eq) and triethylamine (2.0 eq) in dichloromethane (or DMF) (5 mE). The mixture was stirred at 0° C. for 1 hand then at 20° C. overnight. The reaction was concentrated in vacuo to a residue and then purified by reverse-phase (C- 18) liquid chromatography using water and acetonitrile as eluents to yield compound (6). MS (ESI): mlz 329.1 (M+H)+. |