Benzyl Bromide → 2-Benzyl-5-butyl-4-[4-[(1-carboxy)(1-(2-chlorophenyl))methoxy]phenyl]methyl-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 257847Notes

Reaction equation

HRID 257847 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH:19]([C:27]([O:29]C)=[O:28])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])=[CH:14][CH:13]=2)[C:7](=[O:10])[NH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].[CH2:33](Br)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CN(C=O)C>[CH2:33]([N:8]1[C:7](=[O:10])[N:6]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH:19]([C:27]([OH:29])=[O:28])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])=[CH:14][CH:13]=2)[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:9]1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 19781890HCID 19781890, compound

Product 1

HCID 197818302-Benzyl-5-butyl-4-[4-[(1-carboxy)(1-(2-chlorophenyl))methoxy]phenyl]methyl-2,4-dihydro-3H-1,2,4-triazol-3-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the above ester (Step G), sodium hydride (3 equivalents), and dry DMF is stirred under N2 at room temperature for 2 hours. Next, benzyl bromide (5 equivalents) is added, and stirring at room temperature is continued for an additional 1.5 hours or until TLC indicates complete reaction. The mixture is quenched by cautious addition of sufficient acetic acid to destroy the excess sodium hydride and then partitioned between ethyl acetate and H2O. The ethyl acetate phase is washed repeatedly with H2O, then dried (Na2SO4), filtered, and concentrated in vacuo. Chromatography of the residue on silica gel affords the title compound.

Workup

  1. stirringstirring at room temperature
  2. waitis continued for an additional 1.5 hours or until TLC
  3. customreaction
  4. customThe mixture is quenched by cautious addition of sufficient acetic acid
  5. customto destroy the excess sodium hydride
  6. custompartitioned between ethyl acetate and H2O
  7. washThe ethyl acetate phase is washed repeatedly with H2O
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9febca264e064b8892b66ae88c3afc2e
Source dataset
uspto-grants-1993_11
Patent number
US05264439

Reaction notes

Loading…