Water → HCID 58542078, compound

HRID 1966712Notes

Reaction equation

HRID 1966712 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4](F)[CH:3]=1.[NH:11]1[CH:15]=[N:14][CH:13]=[N:12]1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 27249084-Chloro-2-fluorobenzaldehyde

Product 1

HCID 58542078HCID 58542078, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

In a microwave reaction vessel are combined 4-chloro-2-fluoro-benzaldehyde (200 mg. 1.26 mmol), 1H-1,2,4-triazole (113 mg, 1.64 mmol) and potassium carbonate (350 mg, 2.52 mmol) in DMSO (5 mL) and warmed to 80° C. for 5 minutes in a microwave. The reaction mixture is cooled to room temperature and poured into water and extracted with EtOAc (3×). The combined organics are dried (MgSO4), filtered and concentrated. Purification via flash chromatography (12 g silica gel, 0-3% MeOH/CH2Cl2) affords 4-chloro-2-1,2,4-triazol-1-yl-benzaldehyde which is used without further purification.

Workup

  1. customIn a microwave reaction vessel
  2. temperatureThe reaction mixture is cooled to room temperature
  3. extractionextracted with EtOAc (3×)
  4. dry with materialThe combined organics are dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification via flash chromatography (12 g silica gel, 0-3% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-787ab3098d604463a4b5ad198f3500ea
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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