28721-08-6

Basic information

• Product Name: 10-Methoxyiminostilbene-5-carbonylchloride
• Synonyms: 10-Methoxyiminostilbene-5-carbonylchloride;10-METHOXY-5H-DIBENZ[B,F]AZEPINE-5-CARBONYL CHLORIDE;10-Methoxy Iminostilbene Carbonylchloride;N-(2,6-dimethylphenyl)-2-(2-methoxyethylamino)acetamide;N-(2,6-dimethylphenyl)-2-(2-methoxyethylamino)ethanamide;10-Methoxy-5H-dibenzo[b,f]azepine-5-carbonyl chloride;Oxcarbazepine Impurity 9;Oxcarbazepine EP impurity F
• CAS NO: 28721-08-6
• Molecular Formula: C₁₆H₁₂ClNO₂
• Molecular Weight: 285.72
• EINECS: 1533716-785-6
• Mol File: 28721-08-6.mol

Chemical Properties

• Boiling Point: 470.441 °C at 760 mmHg
• Flash Point: 238.315 °C
• Appearance: /
• Density: 1.35
• Storage Temp.: 2-8°C
• PKA: -4.53±0.40(Predicted)
• CAS DataBase Reference: 10-Methoxyiminostilbene-5-carbonylchloride(CAS DataBase Reference)
• NIST Chemistry Reference: 10-Methoxyiminostilbene-5-carbonylchloride(28721-08-6)
• EPA Substance Registry System: 10-Methoxyiminostilbene-5-carbonylchloride(28721-08-6)

Safety Data

• Hazardous Substances Data: 28721-08-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
10-Methoxyiminostilbene-5-carbonylchloride is used as an impurity in the production of Oxcarbazepine, a metabolite of Eslicarbazepine acetate. 10-Methoxyiminostilbene-5-carbonylchloride plays a role in the development and manufacturing process of anticonvulsant medications, which are crucial for treating various seizure disorders and epilepsy.

Upstream product

• 4698-11-7 10-methoxy-5H-dibenzo[b,f]azepine 
• 32315-10-9 bis(trichloromethyl) carbonate 

Downstream Products

• 28721-09-7 10-methoxy-5H-dibenz[b,f]azepine-5-carboxamide 

Relevant articles and documents

RECEPTOR ANTAGONIST, PHARMACEUTICAL COMPOSITION COMPRISING SAME, AND USAGE THEREOF

The present invention discloses a receptor inhibitor of formula (I), a composition comprising the same and the usage thereof.

Synthesis and characterization of potential impurities of Oxcarbazepine drug substance: An antiepileptic agent

Oxcarbazepine is a drug substance used to treat epilepsy. During its bulk synthesis of various impurities formation will be observed. Herein we describe the formation, synthesis and characterization of four potential impurities, namely, N-acetyl Oxcarbazepine, N-formyl Oxcarbazepine, N-carbamoyl Oxcarbazepine, and Oxcarbazepine dimer. These impurities are listed in several Pharmacopoeias and the control of these impurities below the threshold level is essential. Our study will be a guide for making these reference standards.

NOVEL PROCESS FOR PREPARATION OF 10-OXO-10, 11-DIHYDRO-5H-DIBENZ [b,f]AZEPINE-5-CARBOXAMIDE (OXCARBAZEPINE) VIA INTERMEDIATE, 10-METHOXY-5H-DIBENZ[b,f] AZEPINE-5-CARBONYLCHLORIDE

Novel process for preparation of 10-oxo-10, 11-dihydro-SH-dibenz[b,f] azepine-5--carboxamide (oxcarbazepine) via intermediate 10-methoxy-5H--dibenz [b,f] azepine -5 carbonyl, chloride; comprising the steps: a) Preparation of an intermediate 10-methoxy-5H-dibenz [b,f] azepine -5 carbonyl, chloride from 10-methoxyiminostillbene using bis (trichloromethyl) carbonate (BTC) with organic base such as aliphatic or aromatic tertiary amines in organic solvent b) Conversion of the intermediate to 10-methoxy-5H-dlbenz[b,f] azepine -5-- carboxamide using ammonia in organic solvent c) Formation of oxcarbazepine from step(b) using Lewis acid in an organic solvent at a temperature between 25°C - 80°C, preferably at 50°C to 70°C d) Isolation of oxcarbazepine.

PROCESS FOR PREPARING OXCARBAZEPINE

Process for preparing oxcarbazepine according to Scheme 1: characterized by the use of triphosgene as chlorocarbonylating agent in step a).

Process for the preparation of oxcarbazepine

The reaction between 10-methoxy-iminostilbene (IV) and of(trichloromethyl)carbonate affords 10-methoxy-N-chlorocarbonyliminostilbene (XVI) in high yields, then ammonolysis and subsequent hydrolysis of the enol ether provides particularly pure oxcarbazepine.