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

HRID 2234858Notes

Reaction equation

HRID 2234858 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 93.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.4 g (11.6 mmol) of triazine 2a and 7 ml (106 mmol) of acrylonitrile are placed in 24 ml of a solution of pyridine and water (1:1) at reflux for 3 h. After concentration the reaction medium is extracted by AcOEt, and after drying on MgSO4 the organic phases are dry concentrated. 2.8 g of solid 3a are isolated and then washed with ether (yield=93%). TLC silica gel 60 F 254 Merck, petroleum ether:AcOEt 70:30, Rf=0.18.

Workup

  1. temperatureat reflux for 3 h
  2. concentrationAfter concentration the reaction medium
  3. extractionis extracted by AcOEt
  4. customafter drying on MgSO4 the organic phases
  5. customare dry
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a938792dac9a4f6bb9b9d04e564ddbdf
Source dataset
uspto-grants-2010_05
Patent number
US07713971B2

Reaction notes

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