Dimethyl Sulfoxide → 5-Chloro-2-(1H-1,2,4-triazol-1-yl)benzaldehyde

HRID 1481293Notes

Reaction equation

HRID 1481293 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[CH:7]=[O:8].[N:11]1[N:12]=[CH:13][NH:14][CH:15]=1.C([O-])([O-])=O.[Cs+].[Cs+].CS(C)=O>CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 27735865-Chloro-2-fluorobenzaldehydeHCID 178420924HCID 178420924, compound

Product 1

HCID 846756935-Chloro-2-(1H-1,2,4-triazol-1-yl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

To a reaction vessel was added 5-chloro-2-fluorobenzaldehyde (1.29 g, 7.89 mmol), 4H-1,2,4-triazole (0.574 g, 7.89 mmol), Cs2CO3 (2.83 g, 8.68 mmol) and DMSO (15.78 ml). The mixture was capped and heated at 45° C. for 4 hrs before cooling down to rt and stirred at rt over weekend. The reaction mixture was diluted with EtOAc, washed with water and brine, dried over MgSO4, filtered, concentrated and purified by flash chromatography to yield 71A as white solid product (674 mg, 41%). 1H NMR (500 MHz, DMSO-d6) δ 9.90 (s, 1H), 9.17 (s, 1H), 8.33 (s, 1H), 7.99-7.91 (m, 2H), 7.84 (d, J=8.5 Hz, 1H).

Workup

  1. customThe mixture was capped
  2. temperaturebefore cooling down to rt
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-472d67cddef14a5e8b32c755d8e1dd19
Source dataset
uspto-grants-2016_08
Patent number
US09409908B2

Reaction notes

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