Potassium Carbonate → HCID 86660009, compound

HRID 1966690Notes

Reaction equation

HRID 1966690 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:10][C:11]1[N:15]=[CH:14][NH:13][N:12]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[CH3:10][C:11]1[N:15]=[CH:14][N:13]([C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])[N:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67970o-FluorobenzaldehydeHCID 178433329HCID 178433329, compound

Product 1

HCID 86660009HCID 86660009, compoundYield 9.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-fluorobenzaldehyde (400 mg, 3.22 mmol) in DMSO (10 mL) are added 3-methyl-1H-1,2,4-triazole (321 mg, 3.87 mmol) and K2CO3 (890 mg, 6.45 mmol) at room temperature. The solution is heated to 100° C. for 2 hours. The solution is cooled down and extracted with H2O (10 mL) and EtOAc (3×10 mL). The combined organic layer is dried (MgSO4), filtered and concentrated. The residue is purified by silica gel chromatography eluting with 50% EtOAc in heptane as the eluent to afford 2-(3-methyl-1,2,4-triazol-1-yl)-benzaldehyde (55 mg, 8%) as a white solid.

Workup

  1. temperatureThe solution is cooled down
  2. extractionextracted with H2O (10 mL) and EtOAc (3×10 mL)
  3. dry with materialThe combined organic layer is dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by silica gel chromatography
  7. washeluting with 50% EtOAc in heptane as the eluent

Sources & evidence

ORD record
ord-5578bdf6f70345a285e6e8fcdc080b7b
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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