Water → HCID 57927348, compound

HRID 889155Notes

Reaction equation

HRID 889155 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:5][NH:4][C:3]1=[O:13].[Br:14][CH2:15][CH2:16][CH2:17]Br.[H-].[Na+].O>CN(C)C=O.C(OCC)(=O)C>[Br:14][CH2:15][CH2:16][CH2:17][N:4]1[C:3](=[O:13])[N:2]([CH3:1])[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:5]1

Participants

7

Reactant 4

HCID 962WaterHCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 30393113H-1,2,4-Triazol-3-one, 2,4-dihydro-4-methyl-5-phenyl-

Product 1

HCID 57927348HCID 57927348, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

After dissolving 4-methyl-5-phenyl-2,4-dihydro[1,2,4]triazol-3-one (CAS 50369-39-6) (500 mg) and 1,3-dibromopropane (0.87 ml) in N,N-dimethylformamide (9 ml), sodium hydride (60% in oil) (125 mg) was added and the mixture was stirred at room temperature for 6 hours. Water was added to the reaction mixture, and extraction was performed with ethyl acetate. The organic layer was washed with water and brine in that order and then dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (649 mg).

Workup

  1. additionwas added
  2. washThe organic layer was washed with water and brine in that order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d68c2bf347574b2bac1785f445507347
Source dataset
uspto-grants-2012_08
Patent number
US08252810B2

Reaction notes

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