28721-09-7

Basic information

• Product Name: 10-Methoxycarbamazepine
• Synonyms: 10-methoxy-5h-dibenz(b,f)azepine-5-carboxamide;10-METHOXY CARBAMAZEPINE;10-METHOXY-5H-DIBENZ[B,F]AZEPINE-5-CARBOXAMIDE 98.5%;10-Methoxy-5H-dibenzo[b,f]azepine-5-carboxaMide;Oxcarbazepine IMpurity C;Oxcarbazepine Impurity 6
• CAS NO: 28721-09-7
• Molecular Formula: C₁₆H₁₄N₂O₂
• Molecular Weight: 266.29
• EINECS: 249-189-3
• Product Categories: Amines;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 28721-09-7.mol

Chemical Properties

• Melting Point: 186-188°C
• Boiling Point: 468 °C at 760 mmHg
• Flash Point: 236.8 °C
• Appearance: Off-white solid
• Density: 1.31
• Vapor Pressure: 6.21E-09mmHg at 25°C
• Refractive Index: 1.683
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 13.86±0.40(Predicted)
• CAS DataBase Reference: 10-Methoxycarbamazepine(CAS DataBase Reference)
• NIST Chemistry Reference: 10-Methoxycarbamazepine(28721-09-7)
• EPA Substance Registry System: 10-Methoxycarbamazepine(28721-09-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 28721-09-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
10-Methoxycarbamazepine is used as an intermediate in the synthesis of dibenzazepine derivatives for their potential therapeutic applications in the pharmaceutical industry. These derivatives may possess various pharmacological properties, making them valuable in the development of new drugs and treatments.
Used in Chemical Research:
10-Methoxycarbamazepine is used as a research compound in chemical studies, allowing scientists to explore its properties and potential applications in various chemical processes. Its off-white solid form and intermediate role in the synthesis of dibenzazepine derivatives make it a useful tool for researchers in the field.

InChI:InChI=1/C16H14N2O2/c1-20-15-10-11-6-2-4-8-13(11)18(16(17)19)14-9-5-3-7-12(14)15/h2-10H,1H3,(H2,17,19)

Upstream product

• 590-28-3 potassium cyanate 
• 4698-11-7 10-methoxy-5H-dibenzo[b,f]azepine 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 232951-82-5 9-fluorenylmethoxycarbonyl isocyanate 
• 3335-98-6 1-phenyl-1,3-dihydro-indol-2-one 
• 28721-08-6 10-methoxyiminostilbene carbonyl chloride 
• 731851-94-8 10-methoxy-dibenzo[b,f]azepine-5-carboxylic acid phenyl ester 
• 353497-35-5 2-[(methoxycarbonyl)phenylamino]benzeneacetic acid 
• 353497-37-7 10-methoxy-5H-dibenz[b,f]azepine-5-carboxylic acid methyl ester 
• 805236-74-2 [2-(methoxycarbonyl-phenyl-amino)-phenyl]-acetic acid methyl ester 
• 353497-31-1 10,11-dihydro-10-oxo-5H-dibenz[b,f]azepine-5-carboxylic acid methyl ester 
• 39507-06-7 (2-phenylamino-phenyl)-acetic acid methyl ester 
• 917-61-3 sodium isocyanate 

Downstream Products

• 28721-07-5 oxcarbazepine 

Relevant articles and documents

Freezing the Butterfly Motion of Carbamazepine Derivatives

Atropisomeric properties were found in carbamazepine derivatives. The atropisomers of N-acyl and N-thiocarbamoyl derivatives of carbamazepine were isolated, with high stereochemical stability. It has been elucidated that the rotation about the N-C1′ axis around the outer amide N-(C=O) does not coordinate with the rotation of the butterfly-like motion.

PROCESS FOR THE PREPARATION OF OXCARBAZEPINE

The present invention relates to an improved process for the preparation of 10-oxo-10,11-dihydiO-5H-dibenz[b,fjazepine-5-carboxamide (Oxcarbazepine) by reacting 10-methoxy-5H-dibenz[b,f]azepine (10-methoxyiminostilbene) and alkali metal cyanate in presence of α-hydroxy acids, and also relates to the process for the preparation of carbamazepine from iminostilbene. Further the present invention is directed to the novel crystalline form of 10-methoxy carbamazepine.

AN IMPROVED PROCESS FOR THE PREPARATION OF OXCARBAZEPINE

The present invention relates to an improved process for the preparation of 10-oxo- 10,l l-dihydiO-5H-dibenz[b,fjazepine-5-carboxamide (Oxcarbazepine) by reacting 10-methoxy-5H-dibenz[b,f]azepine (10-methoxyiminostilbene) and alkali metal cyanate in presence of α-hydroxy acids, and also relates to the process for the preparation of carbamazepine from iminostilbene. Further the present invention is directed to the novel crystalline form of 10-methoxy carbamazepine.

PROCESS FOR PRODUCING OXCARBAZEPINE VIA AN 11-ALKOXY-10-HALO-DIHYDROIMINOSTILBENE INTERMEDIATE

Disclosed herein is an economically viable and cost effective process for preparation of oxcarbazepine of formula (I) via a novel intermediate of formula (XVIII).

A new industrial process for oxcarbazepine

A novel industrial process for the antiepileptic drug oxcarbazepine 1 has been developed. Unlike the old process, the new process is free from halogenated solvents and can be performed in standard production equipment. It starts from commercially available 1,3-dihydro-1-phenyl-2H-indol-2-one 10. In the key step, an electrophilic ring closure reaction of 2-[(methoxycarbonyl)phenylamino] benzeneacetic acid 5 to 10,11-dihydro-10-oxo-5H-dibenz[b,f]azepine-5-carboxylic acid methyl ester 6 in poly phosphoric acid was applied. For the manufacture of 5, a highly efficient process using a dianion strategy was developed.

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.

Process for the preparation of carboxamide compounds

A process for preparing 5H-dibenz[b,f]azepine-5-carboxamide of the general formula: wherein R1, R2, R3 and R4 are the same or different and can be hydrogen, halogen, nitro, cyano, carboxyl, R, —CO(R), —OCO(R), —O(R), —N(R)2, —CON(R)2, and —COO(R), wherein R is selected from the group consisting of C1-C10 alkyl, C3-C10 cycloalkyl, C2-C10 alkenyl, C5-C10 cycloalkenyl, C2-C10 alkynyl, and C6-C20 aryl, wherein the two A groups of —N(A)2 and —CON(A)2 can be the same or different, and wherein R2 and R3 can together form a bond is provided; the process comprising reacting 5H-dibenz[b,f]azepine of the general formula wherein R1, R2, R3 and R4 have the aforementioned meanings, with one or more alkali or alkaline-earth cyanates and in the presence of one or more unsaturated dicarboxylic acids.

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).

A new synthesis of oxcarbazepine using a Friedel-Crafts cyclization strategy

A novel, simple, and straightforward process for the large-scale synthesis of oxcarbazepine, the active ingredient of Trileptal, a medicine for the treatment of epilepsy, has been developed. Starting from readily available 1,3-dihydro-1-phenyl-2H-indol-2-one, a Friedel-Crafts cyclization strategy provides a direct route to the tricyclic framework of the target molecule. Crucial to the success of the strategy was the choice of the proper nitrogen-protecting group.