Ethanol → 3-(2,6-Difluorophenyl)-6-methyl-[1,2,4]triazine

HRID 2085925Notes

Reaction equation

HRID 2085925 reaction equation
[CH3:1]C(C=O)=O.C(OC([NH:13][NH:14][C:15]([C:17]1[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=1[F:24])=[NH:16])=O)(C)(C)C.[CH2:25](O)[CH3:26]>>[F:24][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]([F:23])[C:17]=1[C:15]1[N:14]=[N:13][C:25]([CH3:26])=[CH:1][N:16]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 880MethylglyoxalHCID 178454364HCID 178454364, compound

Product 1

HCID 227270203-(2,6-Difluorophenyl)-6-methyl-[1,2,4]triazine

Procedure

1.89 g of methylglyoxal (40% in water) are added to 2.71 g of N′-[(2,6-difluorophenyl)-iminomethyl]-hydrazinecarboxylic acid tert-butyl ester in 30 ml of ethanol and stirring is carried out at room temperature for 16 h. The reaction mixture is then concentrated, and the residue is taken up in 20 ml of formic acid and stirring is continued at room temperature for 5 h. The reaction mixture is concentrated by evaporation; the residue is again dissolved in 20 ml of ethanol, boiled under reflux for 2 h, then concentrated and purified by means of column chromatography. In this way 3-(2,6-difluorophenyl)-6-methyl-[1,2,4]triazine having a melting point of 90-93° C. is obtained.

Workup

  1. concentrationThe reaction mixture is then concentrated
  2. stirringstirring
  3. waitis continued at room temperature for 5 h
  4. concentrationThe reaction mixture is concentrated by evaporation
  5. dissolutionthe residue is again dissolved in 20 ml of ethanol
  6. temperatureunder reflux for 2 h
  7. concentrationconcentrated
  8. custompurified by means of column chromatography

Sources & evidence

ORD record
ord-3da89dad3b164d138b7a492d14a6e5f3
Source dataset
uspto-grants-2004_04
Patent number
US06723720B2

Reaction notes

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