Cesium carbonate → 3-(1H-1,2,3-triazol-1-yl)benzaldehyde

HRID 594250Notes

Reaction equation

HRID 594250 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[NH:11]1[CH:15]=[CH:14][N:13]=[N:12]1.CN[C@@H]1CCCC[C@H]1NC.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.[Cu]I.O>[N:11]1([C:2]2[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=2)[CH:5]=[O:7])[CH:15]=[CH:14][N:13]=[N:12]1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 120603-Iodobenzoic acidHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 178418936HCID 178418936, compound

Product 1

HCID 834815293-(1H-1,2,3-triazol-1-yl)benzaldehyde

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

In a sealed tube, a mixture of 3-iodobenzoic acid (2.000 g; 8.06 mmol), 1H-1,2,3-triazole (1.113 g; 16.12 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (236 mg; 1.61 mmol), Cs2CO3 (5.362 g; 16.12 mmol), and CuI (76 mg; 0.40 mmol) in anh. DMF (10 ml) was heated to 120° C. for 16 h. After cooling to rt, water was added, and the mixture was extracted with AcOEt. The separated aq. layer was acidified with aq. 1 M HCl, and extracted with AcOEt (3×). The mixed organic layers were dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH/AcOH=20/1/0.1) afforded the two pure isomers:

Workup

  1. temperatureAfter cooling to rt
  2. extractionthe mixture was extracted with AcOEt
  3. extractionextracted with AcOEt (3×)
  4. dry with materialThe mixed organic layers were dried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customPurification by FC (DCM/MeOH/AcOH=20/1/0.1)
  8. customafforded the two pure isomers

Sources & evidence

ORD record
ord-3b2dffa4edc14773ae1596fc3e5c9df9
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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