Acetic Acid → 2-(Benztriazol-1-ylmethylamino)-4-dimethylamino-6-methoxy-1,3,5-triazine

HRID 34867Notes

Reaction equation

HRID 34867 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]([CH3:10])[CH3:9])[N:5]=[C:4]([O:11][CH3:12])[N:3]=1.[NH:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[N:14]1.C=O.[C:24](O)(=O)C>C(O)C>[N:13]1([CH2:24][NH:1][C:2]2[N:7]=[C:6]([N:8]([CH3:9])[CH3:10])[N:5]=[C:4]([O:11][CH3:12])[N:3]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[N:14]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 7932556-Methoxy-N2,N2-dimethyl-1,3,5-triazine-2,4-diamineHCID 178418385HCID 178418385, compound

Product 1

HCID 540853822-(Benztriazol-1-ylmethylamino)-4-dimethylamino-6-methoxy-1,3,5-triazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

With stirring, a mixture of 16.9 g (0.1 mole) of 2-amino-4-dimethylamino-6-methoxy-1,3,5-triazine, 12 g (0.1 mole) of benztriazole, 9.4 g (0.11 mole) of aqueous 35% formaldehyde and 1 g of acetic acid in 100 ml of ethanol is heated under reflux for 2 hours. The still hot solution is clarified by filtration and crystals of the title compound precipitate from the cooled solution. The precipitate is filtered with suction and dried, affording 25 g (83% of theory) of crystalline product with a melting point of 222°-224° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 2 hours
  3. filtrationThe still hot solution is clarified by filtration and crystals of the title compound precipitate from the cooled solution
  4. filtrationThe precipitate is filtered with suction
  5. customdried
  6. customaffording 25 g (83% of theory) of crystalline product with a melting point of 222°-224° C.

Sources & evidence

ORD record
ord-b775df867cfc4147bd793883ddefb27e
Source dataset
uspto-grants-1988_08
Patent number
US04764203

Reaction notes

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