Pyridine → 3-(6-Bromo-4-methyl-3,5-dioxo-4,5-dihydro-3H-[1,2,4]triazin-2-yl)-propionitrile

HRID 1917086Notes

Reaction equation

HRID 1917086 reaction equation
[Br:1][C:2]1[C:3](=[O:10])[N:4]([CH3:9])[C:5](=[O:8])[NH:6][N:7]=1.[C:11](#[N:14])[CH:12]=[CH2:13].N1C=CC=CC=1>O>[Br:1][C:2]1[C:3](=[O:10])[N:4]([CH3:9])[C:5](=[O:8])[N:6]([CH2:13][CH2:12][C:11]#[N:14])[N:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7855AcrylonitrileHCID 2605646-bromo-4-methyl-1,2,4-triazine-3,5(2h,4h)-dione

Product 1

HCID 592988283-(6-Bromo-4-methyl-3,5-dioxo-4,5-dihydro-3H-[1,2,4]triazin-2-yl)-propionitrileYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.4 g (11.6 mmol) of the triazine 2a and 7 mL (106 mmol) of acrylonitrile are placed in 24 mL of a solution of pyridine and water (1/1) under reflux for 3 h. After concentration, the reaction medium is extracted with AcOEt and then after drying on MgSO4, the organic phases are dry concentrated. After washing the obtained solid with ether, 2.8 g of intermediate 3a are obtained (yield=93%).

Workup

  1. temperatureunder reflux for 3 h
  2. concentrationAfter concentration
  3. extractionthe reaction medium is extracted with AcOEt
  4. customafter drying on MgSO4
  5. customthe organic phases are dry
  6. concentrationconcentrated
  7. washAfter washing the obtained solid with ether, 2.8 g of intermediate 3a
  8. customare obtained (yield=93%)

Sources & evidence

ORD record
ord-803a33367ddc4a929a00e38948010f7a
Source dataset
uspto-grants-2013_12
Patent number
US08618287B2

Reaction notes

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