2898-08-0

Basic information

• Product Name: 1,3-Dihydro-5-phenyl-1,4-benzodiazepin-2-one
• Synonyms: 2,3-DIHYDRO-5-PHENYL-1H-1,4-BENZODIAZEPIN-2-ONE;1,3-DIHYDRO-5-PHENYL-1,4-BENZODIAZEPIN-2-ONE;1,3-DIHYDRO-5-PHENYL-2H-1,4-BENZODIAZEPIN-2-ONE;5-PHENYL-1,3-DIHYDRO-BENZO[E][1,4]DIAZEPIN-2-ONE;RARECHEM EM WB 0256;5-(Phenyl)-1H-1,4-benzodiazepin-2(3H)-one;Ro-5-2921;5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one
• CAS NO: 2898-08-0
• Molecular Formula: C₁₅H₁₂N₂O
• Molecular Weight: 236.27
• EINECS: 220-781-3
• Product Categories: pharmacetical
• Mol File: 2898-08-0.mol
• Article Data: 30

Chemical Properties

• Melting Point: 170-180 °C
• Boiling Point: 424.4 °C at 760 mmHg
• Flash Point: 210.5 °C
• Appearance: /
• Density: 1.21 g/cm³
• Vapor Pressure: 2.08E-07mmHg at 25°C
• Refractive Index: 1.647
• Storage Temp.: Store at -15°C
• PKA: pKa 4.17/12.49(2% aq. EtOH,t =25) (Uncertain)
• CAS DataBase Reference: 1,3-Dihydro-5-phenyl-1,4-benzodiazepin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dihydro-5-phenyl-1,4-benzodiazepin-2-one(2898-08-0)
• EPA Substance Registry System: 1,3-Dihydro-5-phenyl-1,4-benzodiazepin-2-one(2898-08-0)

Safety Data

• Hazardous Substances Data: 2898-08-0(Hazardous Substances Data)

Usage

General Description

1,3-Dihydro-5-phenyl-1,4-benzodiazepin-2-one, also known as phenazepam, is a psychoactive drug belonging to the benzodiazepine class of medications. It is a potent sedative, anxiolytic, and muscle relaxant. Phenazepam is known for its high potency, long duration of action, and strong sedative effects, making it a potentially dangerous substance when misused or abused. It has been used for the treatment of anxiety, insomnia, and seizures, but it is not commonly prescribed due to its potential for misuse and addiction. It is considered a controlled substance in many countries and is classified as a Schedule IV controlled substance in the United States. Phenazepam has been linked to several cases of overdose and death, and its use should be strictly monitored and regulated by medical professionals.

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)

Synthetic route

N-(2-benzoylphenyl)-2-chloroacetamide (23207-75-2) → 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0)

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 (14439-71-5) → 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0)

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 (23207-75-2) → 3-amino-1,2-dihydro-2-oxo-4-phenylquinoline (23207-85-4) + 3-(2-Benzoyl-phenyl)-imidazolidin-4-one + C33H28N4O4 + 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0)

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 (2185-00-4) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0)

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-azido-N-(2-benzoylphenyl)acetamide → 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0)

Conditions	Yield
With 9-phenyl-9-phosphafluorene; diphenylsilane In 1,4-dioxane at 101℃; for 16h; Inert atmosphere;	88%

chloroacetyl chloride (79-04-9) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0)

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 (598-21-0) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0)

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 (4530-20-5) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0)

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 (2835-77-0) → 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0)

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 (623-33-6) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0)

Conditions	Yield
In pyridine for 3h; Dean-Stark; Molecular sieve; Reflux;	52.5%
With pyridine at 100℃;	34%

hexamethylenetetramine (100-97-0) + N-(2-benzoylphenyl)-2-chloroacetamide (23207-75-2) → 3-(2-Benzoyl-phenyl)-imidazolidin-4-one + C33H28N4O4 + 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0)

Conditions	Yield
With urotropin hydrochloride In methanol; water Heating;	A n/a B n/a C 40%

methoxycarbonylmethylamine (616-34-2) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0)

Conditions	Yield
With pyridine Cyclocondensation;

(2-aminophenyl)(phenyl)methanone (2835-77-0) + Amino-acetic acid 4'-(2-amino-acetoxymethyl)-[2,2']bipyridinyl-4-ylmethyl ester; compound with trifluoro-acetic acid → 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0)

Conditions	Yield
In pyridine Heating;

benzonitrile (100-47-0) + Cp2Zr(isoprene) (1) → 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: BCl3; AlCl3 / 1,2-dichloro-ethane 2: pyridine View Scheme

aniline (62-53-3) + Wang resin-bound styrene 4 → 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: BCl3; AlCl3 / 1,2-dichloro-ethane 2: pyridine View Scheme

C28H37N4O5Pol → 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0) + 1-methyl-2,3-dihydro-2-oxo-5-phenyl-1,4-benzodiazepine (3034-65-9)

Conditions	Yield
With water; trifluoroacetic acid In water for 24h; Reflux; solid phase reaction;

tert-butyl-N-({[2-benzoylphenyl]carbamoyl}methyl)carbamate → 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0)

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

2-Glycylamino-benzophenon (5504-78-9) → 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0)

Conditions	Yield
With ammonium acetate; acetic acid at 20℃;	2.32 g

C16H15N3O3 → 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0)

Conditions	Yield
With acetic acid In dichloromethane for 12h; Reflux;

aniline (62-53-3) → 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0)

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

N-chloroacetyl-aniline (587-65-5) → 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0)

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 (5000-66-8) + 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0) → 1-[2-(2-Chloro-phenyl)-2-oxo-ethyl]-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one (145084-65-7)

Conditions	Yield
With sodium hydroxide; Aliquat 336 In toluene for 6h; Ambient temperature;	100%

bromomethyl 2-methoxyphenyl ketone (31949-21-0) + 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0) → 1-[2-(2-Methoxy-phenyl)-2-oxo-ethyl]-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one (145084-53-3)

Conditions	Yield
With sodium hydroxide; Aliquat 336 In toluene for 6h; Ambient temperature;	100%

2-chloro-6 fluorobenzyl chloride (55117-15-2) + 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0) → 1-(2-chloro-6-fluoro-benzyl)-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one (713518-29-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	100%

bromoacetic acid tert-butyl ester (5292-43-3) + 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0) → tert-butyl 2-(2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e] [1,4] diazepin-1-yl)acetate (149620-85-9)

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; caesium carbonate at 20℃;	98%

bromoethyl acetate (927-68-4) + 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0) → acetic acid 2-(2-oxo-5-phenyl-2,3-dihydrobenzo[e][1,4]diazepin-1-yl)ethyl ester (159586-66-0)

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 (824-94-2) + 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0) → 2,3-dihydro-1-[4-methoxybenzyl]-2-oxo-5-phenyl-1H-1,4-benzodiazepine (174698-35-2)

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 (27578-60-5) + 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0) → 2-(2-piperidin-1-ylethylamino)-5-phenyl-3H-1,4-benzodiazepine

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 (2898-08-0) + 2,4,6-trifluorobenzyl chloride → 5-phenyl-1-(2,4,6-trifluoro-benzyl)-1,3-dihydro-benzo[e][1,4]diazepin-2-one (713518-32-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	94%

methylene chloride (74-87-3) + 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0) → 1-methyl-2,3-dihydro-2-oxo-5-phenyl-1,4-benzodiazepine (3034-65-9)

Conditions	Yield
With sodium hydroxide; Aliquat 336 In toluene at 20 - 25℃; for 4h;	93%

1-methyl-piperazine (109-01-3) + 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0) → 2-(4-methylpiperazin-1-yl)-5-phenyl-3H-1,4-benzodiazepine

Conditions	Yield
With titanium tetrachloride; methoxybenzene In dichloromethane at 100℃; for 1h;	93%

(2-chloroethyl)dimethylamine hydrochloride (4584-46-7) + 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0) → 2,3-dihydro-1-(2-dimethylaminoethyl)-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 (70-11-1) + 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0) → 1,3-dihydro-1-phenacyl-5-phenyl-2H-1,4-benzodiazepin-2-one (145084-40-8)

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 (2898-08-0) → 7-bromo-5-phenyl-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one (2894-61-3)

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 (5162-44-7) + 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0) → 1-(but-3-en-1-yl)-5-phenyl-1H-benzo[e][1,4]diazepin-2-one (328917-83-5)

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 (105-36-2) + 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0) → (2-oxo-5-phenyl-2,3-dihydrobenzo[e][1,4]diazepin-1-yl)acetic acid ethyl ester (497873-44-6)

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%

2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0) → nitrazepam (146-22-5)

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 (1242071-55-1) + 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0) → methyl 2-[2-(2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)benzyl]acrylate

Conditions	Yield
With bromopentacarbonylmanganese(I); sodium acetate In 1,4-dioxane at 80℃; for 16h; Inert atmosphere; Schlenk technique;	85%

N,N,N-(ferrocenylmethyl)trimethylammonium iodide + 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0) → 1,3-dihydro-1-ferrocenylmethyl-5-phenyl-2H-1,4-benzodiazepin-2-one (1350644-53-9)

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] (905718-45-8) + 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0) → 1-(4-nitrophenyl)-5-phenyl-1,3-dihydro-2H-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 (1119-51-3) + 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0) → 1-(pent-4-en-1-yl)-5-phenyl-1H-benzo[e][1,4]diazepin-2-one (328917-81-3)

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 (2898-08-0) → 7-chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-thione (4547-02-8)

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 (51012-65-8) + 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0) → 1,3-dihydro-1-(2'-methylphenacyl)-5-phenyl-2H-1,4-benzodiazepin-2-one (145084-43-1)

Conditions	Yield
With sodium hydroxide; Aliquat 336 In toluene for 6h; Ambient temperature;	78%

Upstream product

• 14439-71-5 2'-benzoyl-2-bromo-acetanilide 
• 100-97-0 hexamethylenetetramine 
• 23207-75-2 N-(2-benzoylphenyl)-2-chloroacetamide 
• 616-34-2 methoxycarbonylmethylamine 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 
• 598-21-0 2-Bromoacetyl bromide 
• 100-47-0 benzonitrile 
• 62-53-3 aniline 
• 79-04-9 chloroacetyl chloride 
• 587-65-5 N-chloroacetyl-aniline 
• 2185-00-4 1,3-oxazolidine-2,5-dione 
• 623-33-6 glycine ethyl ester hydrochloride 
• 4530-20-5 BOC-glycine 
• 5504-78-9 2-Glycylamino-benzophenon 

Downstream Products

• 3034-65-9 1-methyl-2,3-dihydro-2-oxo-5-phenyl-1,4-benzodiazepine 
• 117047-24-2 6-Phenyl-4H-2,5,10b-triaza-benzo[e]azulene-3-carboxylic acid ethyl ester 
• 34099-69-9 1,3-dihydro-5-phenyl-2H-1,4-benzodiazepine-2-thione 
• 256234-99-8 1-methyl-7-trimethylsilylacetylenyo-5-phenyl-1,3-dihydrobenzo[e]-1,4-diazepin-2-one 
• 612525-95-8 7-trimethylsilylacetyleno-5-phenyl-1,3-dihydrobenzo[e]-1,4-diazepin-2-one 
• 174276-56-3 3-amino-2,3-dihydro-1-(2-oxo-2-phenylethyl)-5-phenyl-1H-1,4-benzodiazepin-2-one 
• 145084-49-7 3-Amino-1-(2-oxo-2-pyridin-3-yl-ethyl)-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one 
• 145084-41-9 1,3-dihydro-3-hydroxyimino-1-phenacyl-5-phenyl-2H-1,4-benzodiazepin-2-one 
• 145084-58-8 3-amino-1,3-dihydro-1-(4'-methylphenacyl)-5-phenyl-2H-1,4-benzodiazepin-2-one 
• 145084-55-5 3-Amino-1-(2-oxo-2-m-tolyl-ethyl)-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one 
• 145084-51-1 1-(2-Oxo-2-pyridin-3-yl-ethyl)-5-phenyl-1H-benzo[e][1,4]diazepine-2,3-dione 3-oxime 
• 145084-57-7 1-(2-Oxo-2-m-tolyl-ethyl)-5-phenyl-1H-benzo[e][1,4]diazepine-2,3-dione 3-oxime 
• 145084-60-2 1-(2-Oxo-2-p-tolyl-ethyl)-5-phenyl-1H-benzo[e][1,4]diazepine-2,3-dione 3-oxime 
• 145084-44-2 1-(2-Oxo-2-o-tolyl-ethyl)-5-phenyl-1H-benzo[e][1,4]diazepine-2,3-dione 3-oxime 

Relevant articles and documents

Synthesis and biological evaluation of benzodiazepines containing a pentafluorosulfanyl group

The widely used pentafluorosulfanyl group (SF5) was deployed as a bioisosteric replacement for a chloro-group in the benzodiazepine diazepam (Valium). Reaction of 2-amino-5-pentafluorosulfanyl-benzophenone with chloroacetyl chloride followed by hexamethylenetetramine, in the presence of ammonia, led to 7-sulfurpentafluoro-5-phenyl-1H-benzo[1,4]diazepin-2(3H)-one (2c). The latter was able to undergo a Pd-catalysed ortho-arylation, demonstrating that these highly fluorinated benzodiazepines can be further modified to form more complicated scaffolds. The replacement of Cl by the SF5 group, led to a loss of potency for potentiating GABAA receptor activation, most likely because of a lost ligand interaction with His102 in the GABAA receptor α subunit. Dedicated to Professor Jonathan Williams, an inspirational and humble pioneer, a colleague and mentor in chemistry.

Structure-Activity Relationship Studies of Retro-1 Analogues against Shiga Toxin

High-throughput screening has shown that Retro-1 inhibits ricin and Shiga toxins by diminishing their intracellular trafficking via the retrograde route, from early endosomes to the Golgi apparatus. To improve the activity of Retro-1, a structure-activity relationship (SAR) study was undertaken and yielded an analogue with a roughly 70-fold better half-maximal effective concentration (EC50) against Shiga toxin cytotoxicity measured in a cell protein synthesis assay.

Methods for Treating Cognitive Disorders Using Inhibitors of Histone Deacetylase

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