Ethyl 8-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo(1,5-a)(1,4)benzodiazepine-3-carboxylate

Base Information

• Chemical Name: Ethyl 8-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo(1,5-a)(1,4)benzodiazepine-3-carboxylate
• CAS No.: 78756-33-9
• Molecular Formula: C15H14ClN3O3
• Molecular Weight: 319.743
• UNII: ZRD5QFZ6DV
• DSSTox Substance ID: DTXSID40229273
• Nikkaji Number: J153.928K
• Wikidata: Q83109490
• Pharos Ligand ID: 9ATPV1ADFWM5
• ChEMBL ID: CHEMBL415290
• Mol file: 78756-33-9.mol

Synonyms:Ro 15-3505;RO-15-3505

Chemical Property of Ethyl 8-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo(1,5-a)(1,4)benzodiazepine-3-carboxylate

Chemical Property:

• Vapor Pressure: 2.57E-12mmHg at 25°C
• Boiling Point: 554°Cat760mmHg
• Flash Point: 288.9°C
• PSA: 64.43000
• Density: 1.43g/cm³
• LogP: 2.22590
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 319.0723690
• Heavy Atom Count: 22
• Complexity: 461

Purity/Quality:

99.90% ^*data from raw suppliers

8-CHLORO-5,6-DIHYDRO-5-METHYL-6-OXO-4H-IMIDAZO[1,5-A][1,4]BENZODIAZEPINE-3-CARBOXYLIC ACID ETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C2CN(C(=O)C3=C(N2C=N1)C=CC(=C3)Cl)C
• Uses: 8-Chloro-5,6-dihydro-5-methyl-6-oxo-4H-Imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic Acid Ethyl Ester is an impurity of Flumazenil (F500450), an imidazodiazepine which selectively blocks the central effects of classic benzodiazepines.

Technology Process of Ethyl 8-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo(1,5-a)(1,4)benzodiazepine-3-carboxylate

There total 7 articles about Ethyl 8-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo(1,5-a)(1,4)benzodiazepine-3-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 45.0%

Ethyl isocyanoacetate (2999-46-4) → ethyl 8-chloro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate (78756-33-9)

Guidance literature:

3,4-dihydro-7-chloro-4-methyl-2H-1,4-benzodiazepine-2,5(1H)-dione; With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 ℃; for 0.333333h;

With diethyl chlorophosphate; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

Ethyl isocyanoacetate; With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 - 20 ℃;

Reference yield:

Ethyl isocyanoacetate (2999-46-4) + potassium tert-butylate (865-47-4) + diethyl chlorophosphate (814-49-3) + 3,4-dihydro-7-chloro-4-methyl-2H-1,4-benzodiazepine-2,5(1H)-dione (5973-29-5) → ethyl 8-chloro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate (78756-33-9)

Guidance literature:

With acetic acid; In tetrahydrofuran; N-methyl-acetamide; water; ethyl acetate;

Reference yield:

Ethyl isocyanoacetate (2999-46-4) + C14H18ClN2O5P (1027918-09-7) → ethyl 8-chloro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate (78756-33-9)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at -35 - 20 ℃; Inert atmosphere;

DOI:10.1055/s-0028-1083358

upstream raw materials:

ethyl 2-(methylideneamino)acetate

Ethyl isocyanoacetate

3,4-dihydro-7-chloro-4-methyl-2H-1,4-benzodiazepine-2,5(1H)-dione

potassium tert-butylate