Ethyl oxoacetate → 3-(2,6-difluorophenyl)-[1,2,4]triazin-6(1H)-one

HRID 2085921Notes

Reaction equation

HRID 2085921 reaction equation
C([O:5][C:6]([NH:8][NH:9][C:10]([C:12]1[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=1[F:19])=[NH:11])=O)(C)(C)C.[CH2:20](OC(=O)C=O)C>C1(C)C=CC=CC=1>[F:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([F:18])[C:12]=1[C:10]1[N:11]=[CH:20][C:6](=[O:5])[NH:8][N:9]=1

Participants

4

Reactant 2

HCID 70211Ethyl oxoacetateHCID 178454364HCID 178454364, compound

Product 1

HCID 227270193-(2,6-difluorophenyl)-[1,2,4]triazin-6(1H)-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

At room temperature, 30 g of N′-[(2,6-difluorophenyl)-imino-methyl]-hydrazinecarboxylic acid tert-butyl ester and 23.8 g of glyoxylic acid ethyl ester are stirred in 500 ml of toluene at 70° C. for 4 hours. The reaction mixture is then concentrated, 200 ml of formic acid are added and stirring is continued at room temperature for 5 hours. The reaction mixture is concentrated, and the residue is taken up in 300 ml of ethanol and boiled under reflux for 6 h. After concentration of the reaction mixture and recrystallisation from ethyl acetate there is obtained 3-(2,6-difluorophenyl)-[1,2,4]triazin-6(1H)-one having a melting point of 219-226° C.

Workup

  1. concentrationThe reaction mixture is then concentrated
  2. addition200 ml of formic acid are added
  3. concentrationThe reaction mixture is concentrated
  4. temperatureunder reflux for 6 h
  5. customAfter concentration of the reaction mixture and recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-0591e082b0c342aabed6528a18ccf24c
Source dataset
uspto-grants-2004_04
Patent number
US06723720B2

Reaction notes

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