Benzoyl chloride → HCID 13125206, compound

HRID 875234Notes

Reaction equation

HRID 875234 reaction equation
[CH3:1][N:2]1[CH:6]=[N:5][CH:4]=[N:3]1.[C:7](Cl)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CC#N>[CH3:1][N:2]1[C:6]([C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:14])=[N:5][CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 224591H-1,2,4-Triazole, 1-methyl-

Product 1

HCID 13125206HCID 13125206, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-methyl-1H-1,2,4-triazole (5.0 g, 60.17 mmol, 1 eq.) in 250 ml of MeCN cooled to −5° C. were added Benzoyl chloride (8.45 g, 60.17 mmol, 1 eq.) and TEA (6.39 g, 8.8 ml, 63.18 mmol, 1.05 eq.) dropwise. Upon complete addition the temperature was raised to r.t. and the reaction stirred overnight. The white solid was removed by filtration and the solvent evaporated. The yellow residue was triturated in EtOAc and the white solid removed by filtration. The solvent was evaporated and the resulting brown solid was recrystalised in EtOAc/IPE to give (1-methyl-1H-1,2,4-triazol-5-yl)(phenyl)methanone (6.5 g, 58% yield) as a white solid.

Workup

  1. additionUpon complete addition the temperature
  2. customThe white solid was removed by filtration
  3. customthe solvent evaporated
  4. customThe yellow residue was triturated in EtOAc
  5. customthe white solid removed by filtration
  6. customThe solvent was evaporated
  7. customthe resulting brown solid was recrystalised in EtOAc/IPE

Sources & evidence

ORD record
ord-25cb9dfc72184c4c86bea8f3a42d3022
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

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