2-Chlorodiazepam

Base Information

• Chemical Name: 2-Chlorodiazepam
• CAS No.: 2894-68-0
• Molecular Formula: C16H12 Cl2 N2 O
• Molecular Weight: 319.19
• Hs Code.: 2933990090
• UNII: 070818R7PB
• DSSTox Substance ID: DTXSID30183138
• Nikkaji Number: J47.042B
• Wikipedia: Diclazepam
• Wikidata: Q15408412
• ChEMBL ID: CHEMBL268248
• Mol file: 2894-68-0.mol

Synonyms:2-chlorodiazepam;2H-1,4-benzodiazepin-2-one, 7-chloro-5-(2-chlorophenyl)-1,3-dihydro-1-methyl-;diclazepam;Ro 5-3448

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Chemical Property of 2-Chlorodiazepam

Chemical Property:

• Vapor Pressure: 4.23E-11mmHg at 25°C
• Melting Point: 217-219 oC (dichloromethane ethyl ether )**
• Refractive Index: 1.647
• Boiling Point: 524.6°Cat760mmHg
• PKA: 1.75±0.25(Predicted)
• Flash Point: 271.1°C
• PSA: 32.67000
• Density: 1.35±0.1 g/cm3 (20 oC 760 Torr), Calc.*
• LogP: 3.30780
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 318.0326684
• Heavy Atom Count: 21
• Complexity: 440

Purity/Quality:

Safty Information:

• Pictogram(s): symbol Xn Details
• Hazard Codes: symbol Xn Details
• Statements: 22
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(=O)CN=C(C2=C1C=CC(=C2)Cl)C3=CC=CC=C3Cl
• Description: Diclazepam, also known as 2-chlorodiazepam and chlorodiazepam, is classed in the benzodiazepam family, and is therefore a diazepam analogue.It was first synthesized by Leo Sternbach and his team at Hoffman-La Roche in 1960, but it was not pursued as a pharmaceutical product.Diclazepam dosage, efficacy or safety in humans has never been formally studied. In animals, however, it is known to have very similar effects to flubromazepam and diazepam itself. Its effects include working as an anticonvulsant and anxiolytic, a sedative, a hypnotic, an amnesiac and as a skeletal muscle relaxant. It may have adverse effects such as drowsiness, and cognitive impairments such as short term memory impairment. Diclazepam has been assessed as having an elimination half-life of around 42 hours in most animals. In the body, it undergoes N-demethylation, resulting in the creation of delorazepam. The delorazepam can be detected in the subject’s urine for approximately six days. It also metabolises into lormetazepam (detectable for 19 days) and lorazepam (detectable for 11 days). This suggests that cytochrome P450 enzymes are also engaging in hydroxylation of the compound at the same time as the N-demethylation.

Technology Process of 2-Chlorodiazepam

There total 4 articles about 2-Chlorodiazepam 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: 57.0%

delorazepam (2894-67-9) + methyl iodide (74-88-4) → 7-chloro-5-(2-chlorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one (2894-68-0)

Guidance literature:

delorazepam; With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 0.5h;

methyl iodide; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1021/acs.jmedchem.0c00298

Reference yield:

(2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3,53960-29-5) → 7-chloro-5-(2-chlorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one (2894-68-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium carbonate / dichloromethane; water / 2 h / 0 °C

2.1: ammonia / methanol / 0 - 20 °C

3.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C

3.2: 1 h / 20 °C

With ammonia; sodium hydride; sodium carbonate; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/acs.jmedchem.0c00298

Reference yield:

2-(2-bromo-acetylamino)-5,2'-dichloro-benzophenone (5504-92-7) → 7-chloro-5-(2-chlorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one (2894-68-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: ammonia / methanol / 0 - 20 °C

2.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C

2.2: 1 h / 20 °C

With ammonia; sodium hydride; In tetrahydrofuran; methanol;

DOI:10.1021/acs.jmedchem.0c00298

upstream raw materials:

delorazepam

methyl iodide

(2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone

2-(2-bromo-acetylamino)-5,2'-dichloro-benzophenone

Downstream raw materials:

7-chloro-5-(2-chloro-phenyl)-3-(dimethylamino-methylene)-1-methyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one

Refernces

• 1、 Cortes, Eduardo Cortes,Martinez, Isidro Ebromares,Mellado, Olivia Garcia. "Synthesis and Spectral Properties of 7-Chloro-5-[(o- and p-R1)phenyl]-1-R2-3H-[1,4]benzodiazepin-2-ones". . p. 1189 - 1194. Retrieved 2007/10/03.
• 2、 Liepmann,Milkowski,Zeugner. "Cyclization of N1 aryl N2 aroyl 2 hydroxy 1,3 diaminopropanes in benzodiazepines and benzodiazocines". . p. 501 - 507. Retrieved 2007/10/05.