methyl aziridine-1-carboxylate
aniline
A
ethyleneimine
B
(2-Phenylamino-ethyl)-carbamic acid methyl ester
Conditions | Yield |
---|---|
In ethanol at 18 - 25℃; for 480h; | A n/a B 98% |
1-(phenylaminocarbonyl)aziridine
dimethyl amine
A
ethyleneimine
B
fenuron
Conditions | Yield |
---|---|
In ethanol at 18 - 25℃; for 168h; | A n/a B 94% |
piperidine
methyl aziridine-1-carboxylate
A
ethyleneimine
B
(2-Piperidin-1-yl-ethyl)-carbamic acid methyl ester
Conditions | Yield |
---|---|
In ethanol at 18 - 25℃; for 24h; | A n/a B 92% |
1-(phenylaminocarbonyl)aziridine
methylamine
A
ethyleneimine
B
1-methyl-3-phenylurea
Conditions | Yield |
---|---|
In ethanol at 18 - 25℃; for 168h; | A n/a B 92% |
Conditions | Yield |
---|---|
With ammonia In ethanol at 18 - 25℃; for 24h; | A n/a B 90% |
Conditions | Yield |
---|---|
With 1 M DTPP at 60℃; for 48h; | 90% |
With BNTP In dichloromethane at 40℃; for 24h; | 98 % Chromat. |
With potassium hydroxide; sulfuric acid 1.) 80 deg C, overnight; Multistep reaction; | |
With cesium nitrate; iron nitrate; magnesium nitrate on fluoridated P2O5/SiO2/TiO2 at 370℃; for 8h; Temperature; Reagent/catalyst; Inert atmosphere; chemoselective reaction; |
morpholine
methyl aziridine-1-carboxylate
A
ethyleneimine
B
(2-Morpholin-4-yl-ethyl)-carbamic acid methyl ester
Conditions | Yield |
---|---|
In ethanol at 18 - 25℃; for 24h; | A n/a B 88% |
Conditions | Yield |
---|---|
With ammonia In ethanol at 18 - 25℃; for 168h; | A n/a B 88% |
methyl aziridine-1-carboxylate
dimethyl amine
A
ethyleneimine
B
1-methoxycarbonylamino-2-dimethylaminoethane
Conditions | Yield |
---|---|
In ethanol at 18 - 25℃; for 24h; | A n/a B 82% |
Conditions | Yield |
---|---|
With carbon dioxide; DBN; lithium iodide In toluene at 90℃; for 5h; Inert atmosphere; | 82% |
methyl aziridine-1-carboxylate
A
ethyleneimine
B
(2-Aziridin-1-yl-ethyl)-carbamic acid methyl ester
Conditions | Yield |
---|---|
In ethanol at 18 - 25℃; for 24h; | A n/a B 75% |
Conditions | Yield |
---|---|
With sodium hydroxide In water at 50℃; for 2h; Inert atmosphere; | 75% |
With sodium hydroxide In water at 50℃; for 2.5h; | 74% |
With sodium hydroxide at 50℃; under 25 Torr; for 2h; | 70% |
methyl aziridine-1-carboxylate
isopropylamine
A
ethyleneimine
B
(2-Isopropylamino-ethyl)-carbamic acid methyl ester
Conditions | Yield |
---|---|
In ethanol at 18 - 25℃; for 24h; | A n/a B 72% |
methyl aziridine-1-carboxylate
cyclohexylamine
A
ethyleneimine
B
(2-Cyclohexylamino-ethyl)-carbamic acid methyl ester
Conditions | Yield |
---|---|
In ethanol at 18 - 25℃; for 24h; | A n/a B 63% |
Conditions | Yield |
---|---|
With sodium hydroxide In water Heating; | 60% |
With sodium hydroxide | |
With potassium hydroxide |
methanol
ethanolamine
A
ethyleneimine
B
piperazine
C
1,4-diaza-bicyclo[2.2.2]octane
D
(2-hydroxyethyl)(methyl)amine
Conditions | Yield |
---|---|
With Cs-P-Si mixed-oxide at 300℃; under 750.06 Torr; Title compound not separated from byproducts; | A 37 % Chromat. B n/a C n/a D 6% |
Conditions | Yield |
---|---|
With water; silver(l) oxide | |
With potassium hydroxide | |
With alkaline solution |
Conditions | Yield |
---|---|
With potassium perchlorate In acetic acid at 25℃; Rate constant; | |
With tetramethyl ammoniumhydroxide In water; dimethyl sulfoxide at 17.9℃; Rate constant; Kinetics; Thermodynamic data; var. temp., var. solvents mixtures, var. bases, ΔGa, ΔHa, ΔSa; | |
With ammonium bromide In water; dimethyl sulfoxide at 60.3℃; Thermodynamic data; other halide, ΔH(excit.), ΔG(excit.), ΔS(excit.); |
Conditions | Yield |
---|---|
With water In 1,4-dioxane at 39 - 59℃; Kinetics; | |
With tetramethyl ammoniumhydroxide In water; dimethyl sulfoxide at 31.4℃; Rate constant; Kinetics; Thermodynamic data; var. temp., var. solvents mixtures, var. bases, ΔGa, ΔHa, ΔSa; | |
With ammonium chloride In water; dimethyl sulfoxide at 60.3℃; Thermodynamic data; other halide, ΔH(excit.), ΔG(excit.), ΔS(excit.); |
3-Fluoropyridine
Aziridin-Kation
A
ethyleneimine
B
2-fluoropyridine-H(1+)
Conditions | Yield |
---|---|
Thermodynamic data; |
3-Chloropyridine
Aziridin-Kation
A
ethyleneimine
B
3-chloropyridinium
Conditions | Yield |
---|---|
Thermodynamic data; |
Conditions | Yield |
---|---|
With sodium hydroxide In acetonitrile at 25℃; Rate constant; var. pH (from 13 to neutral); |
amide P,P-bis (1-aziridinyl) N,N-dimethyl phosphinique
A
ethyleneimine
B
dimethyl amine
Conditions | Yield |
---|---|
In water-d2 Mechanism; other aziridinyl phosphoramides, other products; |
Conditions | Yield |
---|---|
With sodium hydroxide In acetonitrile at 25℃; Rate constant; var. pH (from 13 to neutral); |
Conditions | Yield |
---|---|
With sodium hydroxide In acetonitrile at 25℃; Rate constant; var. pH (from 13 to neutral); |
Conditions | Yield |
---|---|
With sodium hydroxide In acetonitrile at 25℃; Rate constant; var. pH (from 13 to neutral); |
Conditions | Yield |
---|---|
With tris-(2-chloro-ethyl)-amine Mechanism; Irradiation; also with propene; rel. rate constants; |
N,N'-Bis(2-oxo-3-oxazolidin-3-ylcarbonyl)-1,6-hexanediamine
A
ethyleneimine
B
dimethylenecyclourethane
C
Acetonitrile oxide
D
trans-nitrosoethylene
Conditions | Yield |
---|---|
at 200 - 600℃; Product distribution; pyrolysis; |
methyl aziridine-1-carboxylate
ethylamine
A
ethyleneimine
B
methyl N-ethylcarbamate
C
(2-Ethylamino-ethyl)-carbamic acid methyl ester
Conditions | Yield |
---|---|
In ethanol at 18 - 25℃; for 24h; | A n/a B 35 % Chromat. C 65 % Chromat. |
ethyleneimine
2-chloro-3,6-diphenyl-3,4-dihydro-1,3,2-oxazophosporin-2-oxide
2-Aziridin-1-yl-3,6-diphenyl-3,4-dihydro-[1,3,2]oxazaphosphinine 2-oxide
Conditions | Yield |
---|---|
In benzene for 0.5h; Ambient temperature; | 100% |
ethyleneimine
2-Chloro-6-phenyl-3-p-tolyl-3,4-dihydro-[1,3,2]oxazaphosphinine 2-oxide
2-(1-Aziridinyl)-6-phenyl-3-(p-tolyl)-3,4-dihydro-1,3,2-oxazaphosphorin-2-oxide
Conditions | Yield |
---|---|
In benzene for 0.5h; Ambient temperature; | 100% |
ethyleneimine
2-Chloro-3-(4-methoxy-phenyl)-6-phenyl-3,4-dihydro-[1,3,2]oxazaphosphinine 2-oxide
2-Aziridin-1-yl-3-(4-methoxy-phenyl)-6-phenyl-3,4-dihydro-[1,3,2]oxazaphosphinine 2-oxide
Conditions | Yield |
---|---|
In benzene for 0.5h; Ambient temperature; | 100% |
ethyleneimine
1-chloroaziridine
Conditions | Yield |
---|---|
With N-chloro-succinimide at 20℃; under 0.1 Torr; | 99% |
With sodium hypochlorite; water at -10℃; | |
With N-chloro-succinimide under 0.001 Torr; Ambient temperature; |
ethyleneimine
3-hydroxy-3-methyl-1-cyano-1-butyne
Conditions | Yield |
---|---|
In chloroform at 10℃; for 2h; | 99% |
ethyleneimine
3-chloro-2-phenyl-1-indenone
3-aziridino-2-phenyl-1-indenone
Conditions | Yield |
---|---|
With triethylamine for 0.5h; | 99% |
ethyleneimine
3-chloro-2-(4-chlorophenyl)-1-indenone
3-aziridino-2-(4-chlorophenyl)-1-indenone
Conditions | Yield |
---|---|
With triethylamine for 0.5h; | 99% |
ethyleneimine
3-chloro-2-(4-methoxyphenyl)-1-indenone
3-aziridino-2-(4-methoxyphenyl)-1-indenone
Conditions | Yield |
---|---|
With triethylamine for 0.5h; | 99% |
ethyleneimine
3-chloro-2-(1-naphthyl)-1-indenone
3-aziridino-2-(1-naphthyl)-1-indenone
Conditions | Yield |
---|---|
With triethylamine for 0.5h; | 99% |
ethyleneimine
diethoxyphosphoryldichloroacetaldehyde
Conditions | Yield |
---|---|
In ethanol at 5 - 10℃; for 1h; Addition; | 99% |
ethyleneimine
1-{2-[1,3-(oxytetraethylenoxy)-3,5,5-trichloro-cyclotriphosphazatrien-1-yl]-aminoethylamino}anthraquinone
Conditions | Yield |
---|---|
With sodium hydroxide In benzene at 20℃; for 21.5h; | 99% |
potassium hexafluorophosphate
ethyleneimine
[C5H5(CO)2Fe(COCH2CH2NH)](1+)*PF6(1-)=[C5H5(CO)2Fe(COCH2CH2NH)]PF6
Conditions | Yield |
---|---|
With catalyst: (BrCH2CH2NH3)Br In acetonitrile addn. of aziridine to soln. of complex and bromide via syringe; stirring for 10 min at 25°C under N2; adding an excess of KPF6; stirringfor 5 min; evapn.; washing (Et2O); extg. (CH2Cl29; filtration through MgSO4; reducing volume until crystn. occured; adding Et2O; keeping at -20°C overnight; crystn.; drying in vac.; elem. anal.; | 99% |
With catalyst: (BrCH2CH2CH2NH3)Br In acetonitrile addn. of aziridine to soln. of complex and bromide via syringe; stirring for 10 min at 25°C under N2; adding an excess of KPF6; stirringfor 5 min; evapn.; washing (Et2O); extg. (CH2Cl29; filtration through MgSO4; reducing volume until crystn. occured; adding Et2O; keeping at -20°C overnight; crystn.; drying in vac.; elem. anal.; | 89% |
ethyleneimine
bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]
[IrCl(Cp(*))(aziridine)2]Cl
Conditions | Yield |
---|---|
In dichloromethane (Ar); 5 equiv. of aziridine added to metal-complex in CH2Cl2; stirred atroom temp. for 2 h; solvent removed in vacuo; purified by stirring in dry n-hexane overnight; decanted; dried in vacuo; elem. anal.; | 99% |
ethyleneimine
bis(N,N-diethylamido)-N1-ethyl(bromo)imidophosphate
Conditions | Yield |
---|---|
In benzene at 10℃; | 98% |
ethyleneimine
8-Methoxy-5-quinolinesulfonyl chloride
N-(8-methoxy-5-quinolylsulfonyl)aziridine
Conditions | Yield |
---|---|
With triethylamine In benzene for 3h; O deg C - 20 deg C; | 98% |
ethyleneimine
Acetic acid 4-[(1S,2R)-2-(4-acetoxy-phenyl)-1-chlorocarbonyl-butyl]-phenyl ester
(2R*,3S*)-1-<2,3-bis(4-acetoxyphenyl)-1-pentanoyl>aziridine
Conditions | Yield |
---|---|
With triethylamine In diethyl ether 1.) -4 deg C, 20 min, 2.) RT, 1 h; | 98% |
ethyleneimine
pentapropylphosphorodiamidimidic bromide
Conditions | Yield |
---|---|
In benzene at 10℃; | 98% |
Conditions | Yield |
---|---|
With caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate In toluene at 100℃; for 24h; | 98% |
Conditions | Yield |
---|---|
In chloroform for 2h; darkness; | 98% |
ethyleneimine
(η5-Cp)Fe(CO)3PF6
[C5H5(CO)2Fe(COCH2CH2NH)](1+)*PF6(1-)=[C5H5(CO)2Fe(COCH2CH2NH)]PF6
Conditions | Yield |
---|---|
sodium bromide In acetonitrile ratio of educts and catalyst: 1:1:1; evapn. in vac. to dryness, extrd. with CH2Cl2, pptd. with ether at -20°C; | 98% |
With catalyst: (nBu)4N(1+)*Br(1-) or (nBu4)N(1+)*I(1-) In acetonitrile ratio of educts and catalyst: 1:1:1; evapn. in vac. to dryness, extrd. with CH2Cl2, pptd. with ether at -20°C; | 98% |
With catalyst: Br(CH2)2NH3(1+)*Br(1-) In acetonitrile ratio of educts and catalyst: 1:1:1; evapn. in vac. to dryness, extrd. with CH2Cl2, pptd. with ether at -20°C; | 98% |
With catalyst: Br(CH2)3NH3(1+)*Br(1-) In acetonitrile ratio of educts and catalyst: 1:1:1; evapn. in vac. to dryness, extrd. with CH2Cl2, pptd. with ether at -20°C; | 98% |
With catalyst: Et3NH(1+)*Br(1-) In acetonitrile ratio of educts and catalyst: 1:1:1; evapn. in vac. to dryness, extrd. with CH2Cl2, pptd. with ether at -20°C; | 98% |
Conditions | Yield |
---|---|
In toluene (Schlenk flask); soln. of Re-complex is cooled to -45°C (CH3CN/CO2), CF3SO3H is added dropwise, after 5 min cyclic amine is added and the cold bath is removed; after 60 min hexane is added with stirring, filtrate is washed with hexane and dried under vacuum, elem. anal.; | 98% |
Conditions | Yield |
---|---|
In dichloromethane anhydrous metal chloride suspd. in dry CH2Cl2; 5 equiv. of aziridine added; stirred overnight at 21°C; filtered off; solvent removed in vacuo; purified by stirring in dry n-hexane overnight at ambient temp.; n-hexane phase removed by decantation; dried in vacuo; elem. anal.; | 98% |
In not given (Ar); mole ratio ZnCl2:ethylenimine = 1:2; soln. of ethylenimine added dropwise to a soln. of ZnCl2 with stirring and cooling to -20°C; stirred for 3-4 h; ppt. sepd.; washed (cold soln.); dried (vac.); elem. anal.; |
ethyleneimine
trans-[bis(aziridine)dichloridopalladium(II)]
Conditions | Yield |
---|---|
In dichloromethane anhydrous metal chloride suspd. in dry CH2Cl2; 2 equiv. of aziridine added; stirred overnight at 21°C; filtered off; solvent removed in vacuo; purified by stirring in dry n-hexane overnight at ambient temp.; n-hexane phase removed by decantation; dried in vacuo; elem. anal.; | 98% |
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran at 0 - 20℃; for 2h; Temperature; | 97.5% |
ethyleneimine
pentabutylphosphorodiamidimic bromide
Conditions | Yield |
---|---|
In benzene at 10℃; | 97% |
ethyleneimine
Conditions | Yield |
---|---|
at 20℃; for 1h; | 97% |
ethyleneimine
4-(bis-methylsulfanyl-methylene)-2-phenyl-5-p-tolyl-2,4-dihydro-pyrazol-3-one
4-<(N-aziridinomethylthio)methylene>-3-(p-methylphenyl)-5-oxo-1-phenyl-Δ2-pyrazoline
Conditions | Yield |
---|---|
In diethyl ether at 0 - 20℃; for 3h; | 97% |
ethyleneimine
Conditions | Yield |
---|---|
With C2H5OH In neat (no solvent) careful addn. of aziridine to solid cis-(Co(NH3)(en)2Br)Br2*H2O under stirring and cooling in a dry ice/acetone bath in N2 atm.; stirring at room temp. for 6 h; pptn. by slow addn. of ethanol and diethyl ether;; filtration; washing with ether; drying in vac. over P2O5; elem. anal.;; | 97% |
ethyleneimine
Conditions | Yield |
---|---|
In tetrahydrofuran reaction under N2: a suspn. of Pt-complex in THF is treated with aziridine at 0°C, removing the ice-bath, warming to room temp., stirring for 5 h; reaction is controlled by IR-spectroscopy, filtn., vac. drying, elem. anal.; | 97% |
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