84689-20-3

Usage

Chemical Properties

Yellow Solid

Uses

Different sources of media describe the Uses of 84689-20-3 differently. You can refer to the following data:
1. 2-(2,3-Dichlorphenyl)-2-(guanidinylimino)acetonitrile (Lamotrigine EP Impurity C) is an intermediate in the synthesis of the drug Lamotrigine (L173250).
2. An intermediate in the synthesis of the drug Lamotrigine (L173250).

InChI:InChI=1/C9H7Cl2N5/c10-6-3-1-2-5(8(6)11)7(4-12)15-16-9(13)14/h1-3H,(H4,13,14,16)/b15-7+

Upstream product

• 77668-42-9 2,3-dichlorobenzoyl cyanide 
• 79-17-4 aminoguanidine 
• 2582-30-1 aminoguanidine bicarbonate 

Downstream Products

• 84057-84-1 lamotrigine 

Relevant academic research and scientific papers

AN IMPROVED PROCESS FOR THE PREPARATION OF LAMOTRIGINE

The present invention relates to an improved process for the preparation of Lamotrigine (I) comprising a step of cyclizing 2-(2,3-Dichlorophenyl)-2-(guanidinoimino)acetonitrile(III) in the presence of an alcohol and an acid.

Process for the preparation of 6-(2,3-dichlorophenyl)-1,2,4-triazine-3,5-diamine, commonly known as lamotrigine

A process for the preparation of 6-(2,3-dichlorophenyl)-1,2,4-triazine-3-5-diamine (lamotrigine) of the formula I: 2,3-Dichloronitrobenzene in C1-C6aliphatic alkanol is hydrogenated at 55-90 psi gas pressure using metal catalyst at 27-35° C. 2,3-Dichloroaniline is diazotised and cyano-de-diazonised with metal cyanide at 65-80° C. 2,3-Dichlorobenzonitrile is hydrolysed and 2,3-dichlorobenzoic acid is chlorinated at 55-130° C. Cyano-de-halogenation of 2,3-dichlorobenzoyl chloride is carried out with a metal cyanide and alkali metal iodide by refluxing in an aprotic solvent under an inert atmosphere. 2,3-Dichlorobenzoyl cyanide is condensed with aminoguanidine bicarbonate in an organic solvent in acidic conditions using catalyst at 90-125° C. followed by insitu cyclisation of the Schiff's base by refluxing in an aliphatic alkanol with base. Crude lamotrigine is purified.

Process for preparing substituted Benzoyl Cyanide Amidinohydrazones

The present invention provides a process for preparing a compound of the general formula (I):wherein R1to R5are independently selected from hydrogen, halogen, C1-6alkyl, C2-6alkenyl, C2-6alkynyl or C1-6alkoxy, all optionally substituted by one or more of halogen, hydroxy and aryl groups, as well as being independently selected from amino, mono- or disubstituted amino, alkenyloxy, acyl, acyloxy, cyano, nitro, aryl and alkylthio groups, which process comprises reacting a compound of the general formula (II):wherein R1to R5are as defined in formula (I), with aminoguanidine bicarbonate in a mixture of a water-soluble solvent and polyphosphoric acid.

Process for preparing substituted benzoyl cyanide amidinohydrazones

The present invention provides a process for preparing a compound of the general formula (I): wherein R1 to R5 are independently selected from hydrogen, halogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl or C1-6 alkoxy, all optionally substituted by one or more of halogen, hydroxy and aryl groups, as well as being independently selected from amino, mono- or disubstituted amino, alkenyloxy, acyl, acyloxy, cyano, nitro, aryl and alkylthio groups, which process comprises reacting a compound of the general formula (II): wherein R1 to R5 are as defined in formula (I), with aminoguanidine bicarbonate in a mixture of a water-soluble solvent and polyphosphoric acid.