1-carboxy-2-imidazolidinone
imidazolidone
Conditions | Yield |
---|---|
In water-d2 at 25℃; Rate constant; Mechanism; | 100% |
Conditions | Yield |
---|---|
With 2-pyrrolidinon; caesium carbonate at 200℃; under 37503.8 Torr; for 2h; Temperature; Pressure; Reagent/catalyst; Solvent; Autoclave; | 99% |
With caesium carbonate at 200℃; under 37503.8 Torr; for 2h; Reagent/catalyst; Temperature; Pressure; Autoclave; | 99% |
at 180℃; under 75007.5 Torr; for 24h; Autoclave; | 96.9% |
methanol
1,1'-(2-oxoimidazolidine-1,3-diyl)bis(propan-1-one)
A
imidazolidone
B
propanoic acid methyl ester
Conditions | Yield |
---|---|
With C17H23BN2O at 50℃; under 760.051 Torr; for 15h; Inert atmosphere; chemoselective reaction; | A 97% B n/a |
Conditions | Yield |
---|---|
In acetonitrile for 8h; Ambient temperature; | 90% |
Conditions | Yield |
---|---|
With sodium methylate In methanol; toluene at 55 - 90℃; for 3h; Temperature; Concentration; Solvent; Time; Inert atmosphere; | 90% |
With sodium methylate In methanol; toluene at 23 - 90℃; for 3h; Inert atmosphere; | 90% |
methanol
carbon dioxide
ethylenediamine
A
imidazolidone
B
1-methyl-2-imidazolidone
Conditions | Yield |
---|---|
With ZnO-KF loaded on γ-Al2O3 at 180℃; under 7500.75 Torr; for 4h; Reagent/catalyst; Temperature; | A 86.3% B n/a |
ethanol
carbon dioxide
ethylenediamine
A
imidazolidone
B
1-ethylimidazolidine-2-one
Conditions | Yield |
---|---|
With ZnO-KF loaded on γ-Al2O3 at 180℃; under 7500.75 Torr; for 4h; | A 82.5% B n/a |
propan-1-ol
carbon dioxide
ethylenediamine
A
imidazolidone
B
1-propyl-2-imidazolidone
Conditions | Yield |
---|---|
With ZnO-KF loaded on γ-Al2O3 at 180℃; under 7500.75 Torr; for 4h; | A 80.5% B n/a |
Conditions | Yield |
---|---|
In methanol at 60℃; for 24h; | 80% |
imidazolidone
Conditions | Yield |
---|---|
With trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane In acetonitrile at 20℃; for 0.583333h; chemoselective reaction; | 80% |
Conditions | Yield |
---|---|
With water for 3h; Heating; | 75% |
With water for 3h; Mechanism; Product distribution; Heating; (15)N-labelled urea, N-alkylated 1,2-diaminoethane, toluene as a moderator; | 75% |
In ethylene glycol at 130 - 180℃; for 6h; | 68.3% |
(-)-3-[2-(S)-(1-amino-3,3,3-trifluoropropyl)]-[4-(R)-phenyl]-oxazolidin-2-one
ethylenediamine
A
imidazolidone
B
2-(1-aminomethyl-2,2,2-trifluoroethylamino)-2-phenylethanol
Conditions | Yield |
---|---|
for 18h; Heating; | A n/a B 75% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; acetic acid at 25℃; for 0.0166667h; | 73% |
With potassium hydroxide; dihydrogen peroxide |
Conditions | Yield |
---|---|
With triethylamine In diethyl ether at 18 - 20℃; for 12h; | 70% |
ethylenediamine
carbonic acid dimethyl ester
A
imidazolidone
B
1-methyl-2-imidazolidone
Conditions | Yield |
---|---|
Stage #1: ethylenediamine; carbonic acid dimethyl ester With aminosulfonic acid at 50℃; for 3h; Green chemistry; Stage #2: at 160℃; for 15h; Green chemistry; | A 70% B n/a |
N-(2-formylaminoethyl)formamide
ethylenediamine
A
imidazolidone
B
N-(2-aminoethyl)formamide
Conditions | Yield |
---|---|
With [Ru(PtBuNNHtBu)H(CO)Cl]; potassium tert-butylate In 1,4-dioxane at 150℃; for 24h; Glovebox; Schlenk technique; Inert atmosphere; | A 67% B 19% |
Conditions | Yield |
---|---|
With 3,7-di([1,1′-biphenyl]-4-yl)-10-(naphthalen-1-yl)-10H-phenoxazine; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h; Reagent/catalyst; Inert atmosphere; Irradiation; Sealed tube; | 65% |
Conditions | Yield |
---|---|
With 1,3,5-trichloro-2,4,6-triazine In water at 1 - 95℃; for 15.5h; Temperature; | A 54.4% B 7.9% |
Conditions | Yield |
---|---|
With 3,3-dimethyldioxirane In methanol; acetone at 25℃; | A 53% B 15% |
Conditions | Yield |
---|---|
Stage #1: carbon monoxide; ethylenediamine With potassium carbonate; sulfur In N,N-dimethyl-formamide at 20℃; under 760 Torr; for 4h; Stage #2: With oxygen In N,N-dimethyl-formamide at 20℃; under 760 Torr; for 2h; | 51% |
With iodine; potassium carbonate; tungsten hexacarbonyl In dichloromethane at 20℃; under 60804.1 Torr; for 24h; | 40% |
With iodine; potassium carbonate; tungsten hexacarbonyl In dichloromethane at 20℃; under 76005.1 Torr; for 24h; | 40% |
With dichloro[2-(β-diphenylphosphinoethyl)pyridine]palladium(II); oxygen In water at 100℃; under 30003 Torr; for 4h; Autoclave; Green chemistry; | 90 %Chromat. |
1-methoxycarbonyl-2-imidazolidinone
A
imidazolidone
B
benzophenone
C
triphenylmethyl alcohol
D
1-benzoyl-2-imidazolidinone
Conditions | Yield |
---|---|
In tetrahydrofuran for 2h; Product distribution; Ambient temperature; other imidazolone substrates; var. ratios; | A 22% B 42% C 15% D 5% |
N-(2-aminoethyl)formamide
A
imidazolidone
B
N-(2-formylaminoethyl)formamide
Conditions | Yield |
---|---|
With [Ru(PtBuNNHtBu)H(CO)Cl]; potassium tert-butylate In 1,4-dioxane at 150℃; for 24h; Glovebox; Schlenk technique; Inert atmosphere; | A 38% B 19% |
methanol
ethylenediamine
A
imidazolidone
B
N-(2-aminoethyl)formamide
Conditions | Yield |
---|---|
With [Ru(PtBuNNHtBu)H(CO)Cl]; potassium tert-butylate In 1,4-dioxane at 150℃; for 24h; Glovebox; Schlenk technique; Inert atmosphere; | A 33% B 18% |
carbon monoxide
ethylenediamine
A
2-imidazoline
B
imidazolidone
C
N-β-aminoethylcarbamic acid
Conditions | Yield |
---|---|
With tetracarbonyl nickel In ethanol at 160℃; for 18h; | A 28% B 10.6% C 31.7% |
With tetracarbonyl nickel In ethanol at 160℃; for 18h; | A 28% B 10.6% C 31.7% |
benzamide
A
imidazolidone
B
benzaldehyde
C
benzonitrile
D
diphenyl acetylene
Conditions | Yield |
---|---|
With titanium In tetrahydrofuran for 20h; Heating; | A 30% B 12% C 15% D 5% |
carbon dioxide
ethylenediamine
acetonitrile
A
imidazolidone
B
N,N'-diacetylethylenediamine
Conditions | Yield |
---|---|
With ZnO-KF loaded on γ-Al2O3 at 180℃; under 7500.75 Torr; for 4h; | A 27% B n/a |
carbon dioxide
ethylenediamine
N,N-dimethyl-formamide
A
imidazolidone
B
N-(2-formylaminoethyl)formamide
Conditions | Yield |
---|---|
With ZnO-KF loaded on γ-Al2O3 at 180℃; under 7500.75 Torr; for 4h; | A 13.8% B n/a |
Conditions | Yield |
---|---|
With (6-di-tert-butylphosphinomethyl-2,2’-bipyridyl)Ru(CO)HCl; potassium tert-butylate In 1,4-dioxane at 150℃; for 24h; Glovebox; Schlenk technique; Inert atmosphere; | 13% |
Conditions | Yield |
---|---|
With nitric acid | 100% |
With dinitrogen pentoxide In carbon dioxide at 0 - 5℃; under 45004.5 - 60006 Torr; for 1h; liquid CO2; | 93% |
With ammonium nitrate; trifluoroacetic anhydride In nitromethane Ambient temperature; | 41% |
Conditions | Yield |
---|---|
With silver hexafluoroantimonate; 2-(di-tert-butylphosphino)-1,1'-biphenylgold(I) chloride In 1,4-dioxane at 60℃; for 24h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 100℃; for 16h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water at 15℃; | 98% |
Conditions | Yield |
---|---|
With sodium sulfite In tetrahydrofuran; methanol; hexane | 98% |
imidazolidone
Conditions | Yield |
---|---|
In acetone ligand was added to soln. of Co salt in acetone; mixt. was stirred for 5min; concd. (vac.); mixt. was stirred for 15 min; filtered; dried with hexane; elem. anal.; | 96% |
imidazolidone
bis(trichloromethyl) carbonate
2-oxoimidazolidine-1-carbonyl chloride
Conditions | Yield |
---|---|
In tetrahydrofuran at 55 - 60℃; for 2h; chloroformylation; | 95.6% |
imidazolidone
N-Methoxymethylmonoaza-15-crown-5 ether
N,N'-(2-Oxotetrahydroimidazol-1,3-diyldimethyl)-bis
Conditions | Yield |
---|---|
In tetrachloromethane for 3h; Heating; | 95% |
Conditions | Yield |
---|---|
With 3,5-bis-trifluromethylphenylboronic acid In 1,3,5-trimethyl-benzene for 24h; Heating; | 95% |
Conditions | Yield |
---|---|
With 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate; palladium diacetate In 1,4-dioxane at 100℃; for 6h; | 95% |
imidazolidone
2-bromoanisole
1,3-bis(2-methoxyphenyl)imidazolidin-2-one
Conditions | Yield |
---|---|
With potassium carbonate; trans-N,N'-dimethylcyclohexane-1,2-diamine; copper(l) iodide In toluene for 24h; Goldberg-Buchwald-Nandakumar reaction; Heating; | 95% |
Conditions | Yield |
---|---|
at 20 - 60℃; for 24h; | 95% |
Conditions | Yield |
---|---|
With 2-(di-tert-butylphosphino)-1,1'-biphenylgold(I) chloride; silver trifluoromethanesulfonate In 1,4-dioxane at 100℃; under 6205.94 Torr; for 20h; Autoclave; | 95% |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water at 15℃; | 94% |
Conditions | Yield |
---|---|
With 3,5-bis-trifluromethylphenylboronic acid In 1,3,5-trimethyl-benzene for 23h; Heating; | 94% |
Conditions | Yield |
---|---|
With hydrogenchloride at 20℃; for 0.5h; | 94% |
Conditions | Yield |
---|---|
With hydrogenchloride at 100℃; for 0.0333333h; microwave irradiation; | 94% |
Conditions | Yield |
---|---|
at 20 - 65℃; for 24h; | 94% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 10℃; for 3h; | 93% |
In 1,2-dichloro-ethane at 70 - 75℃; for 1h; | 41.5 g |
In tetrahydrofuran at 0℃; for 3h; |
Conditions | Yield |
---|---|
With hydrogenchloride at 55℃; for 3h; | 93% |
imidazolidone
chloromethyl trimethyl benzene
epichlorohydrin
N,N'-bis(glycidyl)-ethyleneurea
Conditions | Yield |
---|---|
With sodium hydroxide | 93% |
imidazolidone
3-[1-(4-carbamoyl-2-methylphenyl)-5-(4-iodophenyl)-1H-pyrrol-2-yl]propanoic acid ethyl ester
3-[1-(4-carbamoyl-2-methylphenyl)-5-[4-(2-oxo-imidazolidin-1-yl)phenyl]-1H-pyrrol-2-yl]propionic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: imidazolidone; 3-[1-(4-carbamoyl-2-methylphenyl)-5-(4-iodophenyl)-1H-pyrrol-2-yl]propanoic acid ethyl ester With potassium phosphate; copper(l) iodide; N,N-dimethylethylenediamine In N,N-dimethyl-formamide at 120℃; for 0.333333h; Microwave irradiation; Inert atmosphere; Stage #2: imidazolidone With copper(l) iodide In N,N-dimethyl-formamide at 130℃; for 0.333333h; Microwave irradiation; Inert atmosphere; | 93% |
With copper(l) iodide; potassium phosphate tribasic trihydrate; N,N`-dimethylethylenediamine In N,N-dimethyl-formamide at 120 - 130℃; for 0.666667h; Inert atmosphere; Microwave irradiation; Sealed tube; | 93% |
imidazolidone
1,3-dinitroso-imidazolidin-2-one
Conditions | Yield |
---|---|
With dinitrogen tetroxide impregnated on activated charcoal In dichloromethane at 20℃; for 4.33333h; | 92% |
With cross-linked polyvinylpyrrolidone*N2O4; dinitrogen tetraoxide In dichloromethane at 20℃; for 4h; | 90% |
With nitric acid; sodium nitrite |
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium (0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 44h; | 92% |
Conditions | Yield |
---|---|
With caesium carbonate; palladium diacetate In toluene at 90℃; Buchwald-Hartwig amination; | 92% |
Conditions | Yield |
---|---|
With potassium carbonate; trans-N,N'-dimethylcyclohexane-1,2-diamine; copper(l) iodide In toluene for 24h; Goldberg-Buchwald-Nandakumar reaction; Heating; | 92% |
imidazolidone
7-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
With copper(l) iodide; potassium tert-butylate; (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane In N,N-dimethyl-formamide at 120℃; | 92% |
The 2-Imidazolidinone, with the cas register number 120-93-4, has the IUPAC name of imidazolidin-2-one. This is a kind of colorless acicular crystalline, and is soluble in water and hot ethanol while insoluble in ethyl ether. When store, it should be kept at room temperature.
The characteristics of this chemical are as followings: (1)ACD/LogP: -1.23; (2)ACD/LogD (pH 5.5): -1.23; (3)ACD/LogD (pH 7.4): -1.23; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 5.1; (7)ACD/KOC (pH 7.4): 5.1; (8)#H bond acceptors: 3; (9)#H bond donors: 2; (10)Polar Surface Area: 23.55; (11)Index of Refraction: 1.447; (12)Molar Refractivity: 20.66 cm3; (13)Molar Volume: 77.2 cm3; (14)Polarizability: 8.19× 10-24 cm3; (15)Surface Tension: 30.8 dyne/cm; (16)Density: 1.114 g/cm3; (17)Flash Point: 202.5 °C; (18)Enthalpy of Vaporization: 60.42 kJ/mol; (19)Boiling Point: 358.7 °C at 760 mmHg; (20)Vapour Pressure: 2.5E-05 mmHg at 25°C; (21)Exact Mass 86.048013; (22)MonoIsotopic Mass 86.048013; (23)Topological Polar Surface Area 41.1; (24)Heavy Atom Count 6; (25)Complexity 63.2.
The production method of this chemical is below: It could be produce from the thermocompression of quadrol and carbon dioxide, and it could also be made from the condensation and closed loop of quadrol, urea and water.
As to its usage, it is widely applied in many way. It could be used as the formaldehyde scavenger to remove the formaldehyde in the clear-up fabric, such as 2D-resin, KB resin, UF, melamino-formaldehyde resin, and so on; It could also be used in the fined chemical intermediate and in making resin, plasticizer, spray paint, adhesives, and so on.
You should be cautious while dealing with this chemical. It is irritating to eyes, respiratory system and skin, and may cause inflammation to the skin or other mucous. So you had better take the following instructions. Wear suitable protective clothing, and if in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.
Addtionally, the following datas could be converted inte the molecular structure:
(1)SMILES:O=C1NCCN1
(2)InChI:InChI=1/C3H6N2O/c6-3-4-1-2-5-3/h1-2H2,(H2,4,5,6)
(3)InChIKey:YAMHXTCMCPHKLN-UHFFFAOYAA
Below are the toxicity information of this chemical:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 500mg/kg (500mg/kg) | European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 17, Pg. 235, 1982. |
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