1H-1,2,4-Triazole → 5-Methoxy-2-1,2,4-triazol-1-yl-benzaldehyde

HRID 1966670Notes

Reaction equation

HRID 1966670 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].[NH:12]1[CH:16]=[N:15][CH:14]=[N:13]1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:2]([N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)=[C:3]([CH:6]=1)[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 27348722-Fluoro-5-methoxybenzaldehyde

Product 1

HCID 585418925-Methoxy-2-1,2,4-triazol-1-yl-benzaldehydeYield 20.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-fluoro-5-methoxybenzaldehyde (200 mg, 1.29 mmol) in DMSO (10 mL) are added 1,2,4-triazole (134 mg, 1.95 mmol) and K2CO3 (359 mg, 2.60 mmol) at room temperature. The solution is heated to 100° C. for 2 hours. The solution is cooled and is extracted with H2O (30 mL) and EtOAc (3×15 mL). The combined organic layer is dried with MgSO4 and is filtered. The filtrate is concentrated and the residue is purified by silica gel flash column chromatography with 50% EtOAc in heptane as the eluent to afford 5-methoxy-2-1,2,4-triazol-1-yl-benzaldehyde (53 mg, 20%) as a white foam.

Workup

  1. temperatureThe solution is cooled
  2. extractionis extracted with H2O (30 mL) and EtOAc (3×15 mL)
  3. dry with materialThe combined organic layer is dried with MgSO4
  4. filtrationis filtered
  5. concentrationThe filtrate is concentrated
  6. customthe residue is purified by silica gel flash column chromatography with 50% EtOAc in heptane as the eluent

Sources & evidence

ORD record
ord-892d70ed77a44ebba42cd5daa18731c8
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

Loading…