Melamine → N-(4,6-Diamino-1,3,5-triazin-2-yl)pyridine-3-carboxamide

HRID 866404Notes

Reaction equation

HRID 866404 reaction equation
[N:1]1[C:8]([NH2:9])=[N:7][C:5]([NH2:6])=[N:4][C:2]=1[NH2:3].[C:10](O[C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[N:22][CH:21]=1)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[N:13][CH:12]=1>N1C=CC=CC=1>[C:10]([NH:3][C:2]1[N:4]=[C:5]([NH2:6])[N:7]=[C:8]([NH2:9])[N:1]=1)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[N:13][CH:12]=1.[C:10]([NH:3][C:2]1[N:4]=[C:5]([NH:6][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[N:22][CH:21]=2)[N:7]=[C:8]([NH2:9])[N:1]=1)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[N:13][CH:12]=1

Participants

5

Reactant 2

HCID 7955MelamineHCID 85607Nicotinic anhydride

Product 2

HCID 15572591N-(4,6-Diamino-1,3,5-triazin-2-yl)pyridine-3-carboxamideHCID 155725922,4-Bis(nicotinamido)-6-amino-s-triazine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4.9 g of melamine and 17 g of nicotinic acid anhydride are refluxed in 300 ml of pyridine with stirring for 3 hours. After cooling, the pyridine is removed by evaporation to dryness under vacuum and the residue is washed with 3% aqueous potassium carbonate and then with water. The residue is fractionated and recrystallized from methanol to yield 2-nicotinamido-4,6-diamino-s-triazine [monomicotinoylmelamine], melting point 252° - 254° C in a yield of 2.4 g and 2,4-bis(nicotinamido)-6-amino-s-triazine [dinicotinoylmelamine], melting point 265° - 270° C (dec) in a yield of 0.15 g.

Workup

  1. temperatureAfter cooling
  2. customthe pyridine is removed by evaporation to dryness under vacuum
  3. washthe residue is washed with 3% aqueous potassium carbonate
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-958c5ccd558148ceb45f7e80dbf0c4a7
Source dataset
uspto-grants-1978_07
Patent number
US04098892

Reaction notes

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