Butyl bromide → 4-butyl-2H-[1,2,4]triazine-3,5-dione

HRID 232558Notes

Reaction equation

HRID 232558 reaction equation
[H-].[Na+].C([N:6]1[C:11](=[O:12])[NH:10][C:9](=[O:13])[CH:8]=[N:7]1)(=O)C.Br[CH2:15][CH2:16][CH2:17][CH3:18]>CN(C=O)C>[CH2:15]([N:10]1[C:9](=[O:13])[CH:8]=[N:7][NH:6][C:11]1=[O:12])[CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 24758Sodium hydrideHCID 212565952-Acetyl-1,2,4-triazine-3,5(2H,4H)-dione

Product 1

HCID 152295424-butyl-2H-[1,2,4]triazine-3,5-dioneYield 51.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a 50% sodium hydride suspension (4.8 g) in DMF (100 ml), compound 11a (15.5 g) dissolved in DMF (200 ml) is added drop by drop, maintaining the temperature at room temperature. After agitation for 2 hours, bromobutane (20 g) is added and the agitation continued for 12 hours. The reaction mixture is concentrated to dryness under vacuum at 60° C., taken up in water, and then extracted with methylene chloride. After concentration to dryness under vacuum, the oil is taken up in ethanol (100 ml), whereupon p-toluene-sulfonic acid (2 g) is added. After heating under reflux for 2 hours and leaving at room temperature for 12 hours, the reaction mixture is filtered. The precipitate is washed with an aqueous solution of sodium bicarbonate and water, and then dried in an oven under vacuum in order to give the compound 11b (8.7 g).

Workup

  1. additionis added drop by drop
  2. waitthe agitation continued for 12 hours
  3. concentrationThe reaction mixture is concentrated to dryness under vacuum at 60° C.
  4. extractionextracted with methylene chloride
  5. concentrationAfter concentration to dryness under vacuum
  6. additionwhereupon p-toluene-sulfonic acid (2 g) is added
  7. temperatureAfter heating
  8. temperatureunder reflux for 2 hours
  9. customleaving at room temperature for 12 hours
  10. filtrationthe reaction mixture is filtered
  11. washThe precipitate is washed with an aqueous solution of sodium bicarbonate and water
  12. customdried in an oven under vacuum in order

Sources & evidence

ORD record
ord-6974236b42d44bc78784a6372609c773
Source dataset
uspto-grants-1997_01
Patent number
US05591743

Reaction notes

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