Lamotrigine → Lamotrigine N-Acetate

HRID 1153712

Reaction equation

HRID 1153712 reaction equation
[NH2:1][C:2]1[N:3]=[N:4][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:10]=2[Cl:16])=[C:6]([NH2:8])[N:7]=1.[C:17](OC(=O)C)(=[O:19])[CH3:18]>C(O)(=O)C>[C:17]([NH:8][C:6]1[N:7]=[C:2]([NH2:1])[N:3]=[N:4][C:5]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:10]=1[Cl:16])(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 3878LamotrigineHCID 7918Acetic Anhydride

Product 1

HCID 23311124Lamotrigine N-Acetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine (2 gm, 8 mM) and acetic anhydride (10 mls) in acetic acid (20 mls) was stirred and heated to reflux for 2 hours. The solution was then cooled and evaporated down in vacuo. The residue was treated with aqueous 0.880 ammonia (100 mls) and the resultant mixture was stirred for 2 hours. The solid was separated by filtration, dried then recrystallized from isopropanol to give 5-acetamido-3-amino-6-(2,3-dichlorophenyl)-1,2,4-triazine. Yield 1.0 gms (42%), m.p. 250°-252° C. (uncorrected).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. temperatureThe solution was then cooled
  4. customevaporated down in vacuo
  5. additionThe residue was treated with aqueous 0.880 ammonia (100 mls)
  6. customThe solid was separated by filtration
  7. customdried
  8. customthen recrystallized from isopropanol

Sources & evidence

ORD record
ord-3c8ad30470454cc3891abd2ecd103bb3
Source dataset
uspto-grants-1984_12
Patent number
US04486354

Linked notes

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