Lamotrigine → N-(5-Amino-6-(2,3-dichlorophenyl)-1,2,4-triazin-3-yl)-2,3-dichlorobenzamide

HRID 2270887Notes

Reaction equation

HRID 2270887 reaction equation
[CH:1]1[CH:6]=[C:5]([Cl:7])[C:4]([Cl:8])=[C:3]([C:9]2[N:14]=[N:13][C:12]([NH2:15])=[N:11][C:10]=2[NH2:16])[CH:2]=1.[Cl:17][C:18]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21]>N1C=CC=CC=1>[NH2:16][C:10]1[N:11]=[C:12]([NH:15][C:20](=[O:21])[C:19]2[CH:23]=[CH:24][CH:25]=[C:26]([Cl:27])[C:18]=2[Cl:17])[N:13]=[N:14][C:9]=1[C:3]1[CH:2]=[CH:1][CH:6]=[C:5]([Cl:7])[C:4]=1[Cl:8]

Participants

4

Reactant 2

HCID 3878LamotrigineHCID 179442,3-Dichlorobenzoyl chloride

Product 1

HCID 18329573N-(5-Amino-6-(2,3-dichlorophenyl)-1,2,4-triazin-3-yl)-2,3-dichlorobenzamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Lamotrigine (512.00 g, 2.00 moles) was dissolved in pyridine (3 I) and 2,3-dichlorobenzoyl chloride (873.00 g, 96% pure, equivalent to 838.10 g, 4.00 moles) was added below 35° C. with stirring under anhydrous conditions. The acid chloride was added in two equal portions. The second portion of acid chloride was added after 30 minutes from the start of the reaction and stirred below 35° C. for a further 30 minutes.

Workup

  1. stirringstirred below 35° C. for a further 30 minutes

Sources & evidence

ORD record
ord-7f7da621e3bb47d392787cae534d566f
Source dataset
uspto-grants-2001_12
Patent number
US06333198B1

Reaction notes

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