Sodium Carbonate → HCID 57927301, compound

HRID 889151Notes

Reaction equation

HRID 889151 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[C:4](=[O:7])[NH:5][N:6]=1.[H-].[Na+].[CH2:16]([CH:18]1[O:20][CH2:19]1)Br.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.C(Cl)(Cl)Cl.C(OCC)(=O)C>[CH3:1][C:2]1[N:3]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[C:4](=[O:7])[N:5]([CH2:16][CH:18]2[CH2:19][O:20]2)[N:6]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 18430EpibromohydrinHCID 24758Sodium hydrideHCID 386150HCID 386150, compound

Product 1

HCID 57927301HCID 57927301, compound

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

After dissolving 5-methyl-4-pyridin-3-yl-2,4-dihydro[1,2,4]triazol-3-one (CAS 79369-46-3) (100 mg) in N,N-dimethylformamide (2 ml), sodium hydride (60% in oil) (27 mg) was added and the mixture was stirred at room temperature. Epibromohydrin (73 μl) was then added and the mixture was stirred overnight at room temperature. A saturated aqueous solution of sodium carbonate was added to the reaction mixture, and extraction was performed with ethyl acetate and chloroform. The extract was 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 (136 mg).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred overnight at room temperature
  3. dry with materialThe extract was dried 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-b2bb3a32742d4b208b3f1b6bdf485e3c
Source dataset
uspto-grants-2012_08
Patent number
US08252810B2

Reaction notes

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