N-(2-benzoylphenyl)-2-chloroacetamide
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
Conditions | Yield |
---|---|
With hexamethylenetetramine; ammonium acetate In ethanol for 6h; Reflux; | 95% |
With hexamethylenetetramine In ethanol; chloroform | 86% |
With paraformaldehyde In methanol; toluene | 84.7% |
With hexamethylenetetramine; ammonium chloride In ethanol for 4h; Reflux; | 50% |
Multi-step reaction with 2 steps 1: sodium azide / N,N-dimethyl-formamide / 18 h / 20 °C / Inert atmosphere 2: diphenylsilane; 9-phenyl-9-phosphafluorene / 1,4-dioxane / 16 h / 101 °C / Inert atmosphere View Scheme |
2'-benzoyl-2-bromo-acetanilide
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
Conditions | Yield |
---|---|
With ammonia In methanol Heating; | 90% |
With ammonia In methanol for 2h; Heating; Yield given; | |
With ammonium hydroxide In ethanol Yield given; |
N-(2-benzoylphenyl)-2-chloroacetamide
A
3-amino-1,2-dihydro-2-oxo-4-phenylquinoline
D
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
Conditions | Yield |
---|---|
With hexamethylenetetramine; ammonia In ethanol at 70℃; Further byproducts given; | A n/a B n/a C n/a D 89% |
1,3-oxazolidine-2,5-dione
(2-aminophenyl)(phenyl)methanone
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
Conditions | Yield |
---|---|
Stage #1: 1,3-oxazolidine-2,5-dione; (2-aminophenyl)(phenyl)methanone With trifluoroacetic acid In toluene at 60℃; for 0.5h; Sealed tube; Stage #2: With triethylamine at 80℃; for 0.5h; Sealed tube; | 89% |
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
Conditions | Yield |
---|---|
With 9-phenyl-9-phosphafluorene; diphenylsilane In 1,4-dioxane at 101℃; for 16h; Inert atmosphere; | 88% |
chloroacetyl chloride
(2-aminophenyl)(phenyl)methanone
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
Conditions | Yield |
---|---|
Stage #1: chloroacetyl chloride; (2-aminophenyl)(phenyl)methanone With triethylamine In dichloromethane at 20 - 30℃; for 3h; Stage #2: With ammonia at 25℃; | 84.4% |
With sodium iodide; ammonia; acetic acid In tetrahydrofuran; chloroform; ethyl acetate |
2-Bromoacetyl bromide
(2-aminophenyl)(phenyl)methanone
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
Conditions | Yield |
---|---|
Stage #1: 2-Bromoacetyl bromide; (2-aminophenyl)(phenyl)methanone With sodium hydrogencarbonate In chloroform at 0℃; Stage #2: With ammonia In methanol at 0 - 20℃; Heating / reflux; | 83% |
Stage #1: 2-Bromoacetyl bromide; (2-aminophenyl)(phenyl)methanone In dichloromethane; water Stage #2: With ammonia | |
With sodium hydroxide In dichloromethane |
BOC-glycine
(2-aminophenyl)(phenyl)methanone
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
Conditions | Yield |
---|---|
Stage #1: BOC-glycine; (2-aminophenyl)(phenyl)methanone With dicyclohexyl-carbodiimide In toluene at 150℃; for 0.5h; Microwave irradiation; Stage #2: With trifluoroacetic acid In toluene at 150℃; for 0.333333h; Microwave irradiation; | 83% |
Stage #1: BOC-glycine; (2-aminophenyl)(phenyl)methanone With dicyclohexyl-carbodiimide In toluene at 150℃; for 1.5h; Microwave irradiation; Stage #2: With trifluoroacetic acid In toluene for 0.333333h; | 65% |
Stage #1: BOC-glycine With 4-methyl-morpholine; chloroformic acid ethyl ester In tetrahydrofuran at -20℃; for 0.25h; Stage #2: (2-aminophenyl)(phenyl)methanone With 4-methyl-morpholine In tetrahydrofuran at 20℃; Stage #3: With trifluoroacetic acid In dichloromethane at 0 - 20℃; |
(2-aminophenyl)(phenyl)methanone
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
Conditions | Yield |
---|---|
53% | |
Multi-step reaction with 2 steps 1: NaHCO3 / CH2Cl2 2: 90 percent / NH3 / methanol / Heating View Scheme | |
Multi-step reaction with 2 steps 1: CH2Cl2 2: aq. NH3 / ethanol View Scheme |
glycine ethyl ester hydrochloride
(2-aminophenyl)(phenyl)methanone
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
Conditions | Yield |
---|---|
In pyridine for 3h; Dean-Stark; Molecular sieve; Reflux; | 52.5% |
With pyridine at 100℃; | 34% |
hexamethylenetetramine
N-(2-benzoylphenyl)-2-chloroacetamide
C
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
Conditions | Yield |
---|---|
With urotropin hydrochloride In methanol; water Heating; | A n/a B n/a C 40% |
methoxycarbonylmethylamine
(2-aminophenyl)(phenyl)methanone
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
Conditions | Yield |
---|---|
With pyridine Cyclocondensation; |
(2-aminophenyl)(phenyl)methanone
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
Conditions | Yield |
---|---|
In pyridine Heating; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: BCl3; AlCl3 / 1,2-dichloro-ethane 2: pyridine View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: BCl3; AlCl3 / 1,2-dichloro-ethane 2: pyridine View Scheme |
A
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
B
1-methyl-2,3-dihydro-2-oxo-5-phenyl-1,4-benzodiazepine
Conditions | Yield |
---|---|
With water; trifluoroacetic acid In water for 24h; Reflux; solid phase reaction; |
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: trifluoroacetic acid / dichloromethane / 2.5 h / 20 °C 2: ammonium acetate; acetic acid / 20 °C View Scheme |
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid at 20℃; | 2.32 g |
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
Conditions | Yield |
---|---|
With acetic acid In dichloromethane for 12h; Reflux; |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: pyridine / benzene / 4 h / Reflux 2: aluminum (III) chloride / benzene / 10 h / Reflux 3: ammonium chloride; hexamethylenetetramine / ethanol / 4 h / Reflux View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aluminum (III) chloride / benzene / 10 h / Reflux 2: ammonium chloride; hexamethylenetetramine / ethanol / 4 h / Reflux View Scheme |
2-chlorophenacyl bromide
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
1-[2-(2-Chloro-phenyl)-2-oxo-ethyl]-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one
Conditions | Yield |
---|---|
With sodium hydroxide; Aliquat 336 In toluene for 6h; Ambient temperature; | 100% |
bromomethyl 2-methoxyphenyl ketone
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
1-[2-(2-Methoxy-phenyl)-2-oxo-ethyl]-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one
Conditions | Yield |
---|---|
With sodium hydroxide; Aliquat 336 In toluene for 6h; Ambient temperature; | 100% |
2-chloro-6 fluorobenzyl chloride
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
1-(2-chloro-6-fluoro-benzyl)-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 100% |
bromoacetic acid tert-butyl ester
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
tert-butyl 2-(2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e] [1,4] diazepin-1-yl)acetate
Conditions | Yield |
---|---|
With 1-methyl-pyrrolidin-2-one; caesium carbonate at 20℃; | 98% |
bromoethyl acetate
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
acetic acid 2-(2-oxo-5-phenyl-2,3-dihydrobenzo[e][1,4]diazepin-1-yl)ethyl ester
Conditions | Yield |
---|---|
Stage #1: 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one With sodium hydride In N,N-dimethyl-formamide at 20℃; Stage #2: bromoethyl acetate In N,N-dimethyl-formamide at 20℃; for 2h; | 97% |
p-methoxybenzyl chloride
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
2,3-dihydro-1-[4-methoxybenzyl]-2-oxo-5-phenyl-1H-1,4-benzodiazepine
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; | 95% |
With potassium carbonate In water; ethyl acetate; N,N-dimethyl-formamide | |
Stage #1: 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.333333h; Stage #2: p-methoxybenzyl chloride In N,N-dimethyl-formamide; mineral oil at 0℃; for 3.5h; | 1.262 g |
Stage #1: 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.333333h; Stage #2: p-methoxybenzyl chloride In N,N-dimethyl-formamide; mineral oil at 20℃; for 3.5h; | 1.262 g |
1-(2-aminoethyl)piperidine
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
Conditions | Yield |
---|---|
With titanium tetrachloride; methoxybenzene In dichloromethane at 100℃; for 0.0833333h; microwave irradiation; | 95% |
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
5-phenyl-1-(2,4,6-trifluoro-benzyl)-1,3-dihydro-benzo[e][1,4]diazepin-2-one
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 94% |
methylene chloride
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
1-methyl-2,3-dihydro-2-oxo-5-phenyl-1,4-benzodiazepine
Conditions | Yield |
---|---|
With sodium hydroxide; Aliquat 336 In toluene at 20 - 25℃; for 4h; | 93% |
Conditions | Yield |
---|---|
With titanium tetrachloride; methoxybenzene In dichloromethane at 100℃; for 1h; | 93% |
(2-chloroethyl)dimethylamine hydrochloride
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
Conditions | Yield |
---|---|
With potassium iodide In hexane; water; N,N-dimethyl-formamide; mineral oil | 93% |
With potassium iodide In hexane; water; N,N-dimethyl-formamide; mineral oil | 93% |
With potassium iodide In hexane; water; N,N-dimethyl-formamide; mineral oil | 93% |
α-bromoacetophenone
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
1,3-dihydro-1-phenacyl-5-phenyl-2H-1,4-benzodiazepin-2-one
Conditions | Yield |
---|---|
With sodium hydroxide; Aliquat 336 In toluene for 6h; Ambient temperature; | 90% |
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
7-bromo-5-phenyl-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one
Conditions | Yield |
---|---|
With sulfuric acid; bromine In acetic acid at 20℃; for 48h; | 90% |
With sulfuric acid; bromine In acetic acid | 65.9% |
1-bromo-4-butene
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
1-(but-3-en-1-yl)-5-phenyl-1H-benzo[e][1,4]diazepin-2-one
Conditions | Yield |
---|---|
Stage #1: 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: 1-bromo-4-butene In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere; | 89% |
Stage #1: 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Inert atmosphere; Stage #2: 1-bromo-4-butene In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere; |
ethyl bromoacetate
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
(2-oxo-5-phenyl-2,3-dihydrobenzo[e][1,4]diazepin-1-yl)acetic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide at 20℃; for 1h; | 88% |
Stage #1: 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere; | 64% |
Conditions | Yield |
---|---|
With 3-(ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium bis(trifluoromethanesulfonyl)imide at 20℃; for 5h; Ionic liquid; | 88% |
methyl 2-(((tert-butoxycarbonyl)oxy)methyl)acrylate
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
Conditions | Yield |
---|---|
With bromopentacarbonylmanganese(I); sodium acetate In 1,4-dioxane at 80℃; for 16h; Inert atmosphere; Schlenk technique; | 85% |
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
1,3-dihydro-1-ferrocenylmethyl-5-phenyl-2H-1,4-benzodiazepin-2-one
Conditions | Yield |
---|---|
With potassium tert-butoxide In N,N-dimethyl-formamide under N2; t-BuOK added to soln. of benzodiazepine in freshly distd. DMF at 0°C; stirred at 0°C for 30 min; Fe complex in DMF addedat 20°C; heated at 150°C for 4 h; aq. HCl added until neutralization; extd. by CH2Cl2; org. layers dried (MgSO4); evapd.; purified by column chromy. (ethyl acetate-petroleum ether 5:5); elem. anal.; | 84% |
[(4-nitrophenyl)(phenyl)iodonium trifluoromethanesulfonate]
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
Conditions | Yield |
---|---|
With ammonium hydroxide In 1,2-dichloro-ethane at 20℃; for 0.5h; Solvent; Reagent/catalyst; Inert atmosphere; | 82% |
bromopentene
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
1-(pent-4-en-1-yl)-5-phenyl-1H-benzo[e][1,4]diazepin-2-one
Conditions | Yield |
---|---|
Stage #1: 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: bromopentene In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere; | 81% |
Stage #1: 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Inert atmosphere; Stage #2: bromopentene In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere; |
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
7-chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-thione
Conditions | Yield |
---|---|
Stage #1: 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one With aluminum (III) chloride; chlorine In dichloromethane at 10 - 20℃; Stage #2: With sodiumsulfide nonahydrate; tetrabutylammomium bromide; dihydrogen peroxide for 2h; Reflux; | 78.7% |
2-bromo-1-o-tolylethanone
2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
1,3-dihydro-1-(2'-methylphenacyl)-5-phenyl-2H-1,4-benzodiazepin-2-one
Conditions | Yield |
---|---|
With sodium hydroxide; Aliquat 336 In toluene for 6h; Ambient temperature; | 78% |
Molecular Structure of 1,3-Dihydro-5-phenyl-1,4-benzodiazepin-2-one (CAS No.2898-08-0):
Molecular Formula: C15H12N2O
Molecular Weight: 236.2686
CAS No: 2898-08-0
IUPAC Name: 5-Phenyl-1,3-dihydro-1,4-benzodiazepin-2-one
H bond acceptors: 3
H bond donors: 1
Freely Rotating Bonds: 1
Polar Surface Area: 32.67 Å2
Index of Refraction: 1.647
Molar Refractivity: 70.98 cm3
Molar Volume: 195.2 cm3
Surface Tension: 48.1 dyne/cm
Density: 1.21 g/cm3
Flash Point: 210.5 °C
Enthalpy of Vaporization: 67.89 kJ/mol
Boiling Point: 424.4 °C at 760 mmHg
Vapour Pressure: 2.08E-07 mmHg at 25°C
InChI: InChI=1/C15H12N2O/c18-14-10-16-15(11-6-2-1-3-7-11)12-8-4-5-9-13(12)17-14/h1-9H,10H2,(H,17,18)
InChIKey: IVUAAOBNUNMJQC-UHFFFAOYAK
Std. InChI: InChI=1S/C15H12N2O/c18-14-10-16-15(11-6-2-1-3-7-11)12-8-4-5-9-13(12)17-14/h1-9H,10H2,(H,17,18)
Std. InChIKey: IVUAAOBNUNMJQC-UHFFFAOYSA-N
Product Categories: Pharmacetical
1,3-Dihydro-5-phenyl-1,4-benzodiazepin-2-one (CAS No.2898-08-0), its synonyms are 1,3-Dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one ; 2H-1,4-benzodiazepin-2-one, 1,3-dihydro-5-phenyl- ; 5-Phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one ; 5-Phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one ; 2,3-Dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one
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