Water → HCID 57927538, compound

HRID 889156Notes

Reaction equation

HRID 889156 reaction equation
[C:1]1([N:7]2[CH:11]=[N:10][NH:9][C:8]2=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:13][CH2:14][CH2:15][CH2:16]Br.[H-].[Na+].O>CN(C)C=O.C(OCC)(=O)C>[Br:13][CH2:14][CH2:15][CH2:16][N:9]1[C:8](=[O:12])[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:11]=[N:10]1

Participants

7

Reactant 4

HCID 962WaterHCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 2614194-Phenyl-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 57927538HCID 57927538, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

After dissolving 4-phenyl-2,4-dihydro[1,2,4]triazol-3-one (CAS 1008-30-6) (1.00 g) and 1,3-dibromopropane (1.89 ml) in N,N-dimethylformamide (15 ml), sodium hydride (60% in oil) (273 mg) was added and the mixture was stirred at room temperature for 4 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. The obtained solid was washed with n-heptane to obtain the title compound (840 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
  7. washThe obtained solid was washed with n-heptane

Sources & evidence

ORD record
ord-bb23f3e9d3914fa6884b4da41936638c
Source dataset
uspto-grants-2012_08
Patent number
US08252810B2

Reaction notes

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