Sodium Carbonate → 1-(furan-2-yl)-4-phenyl-1H-1,2,3-triazole

HRID 1476698Notes

Reaction equation

HRID 1476698 reaction equation
Br[C:2]1[O:3][CH:4]=[CH:5][CH:6]=1.[C:7]1([C:13]#[CH:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[Na+].[Na+].[N-:29]=[N+:30]=[N-:31].[Na+].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2].O.CS(C)=O>[O:3]1[CH:4]=[CH:5][CH:6]=[C:2]1[N:29]1[CH:14]=[C:13]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:31]=[N:30]1

Participants

10

Reactant 6

HCID 10340Sodium CarbonateHCID 10821PhenylacetyleneHCID 33557Sodium AzideHCID 145742L-ProlineHCID 2776190Furan, 2-bromo-HCID 23667548Sodium Ascorbate

Product 1

HCID 904121181-(furan-2-yl)-4-phenyl-1H-1,2,3-triazoleYield 5%

Reagents, catalysts & solvents 3

HCID 24463Copper sulfate pentahydrateCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

A stirred solution of 2-bromofuran (500 mg, 3.40 mmol) and phenyl acetylene (347 mg, 3.39 mmol) in a mixture of solvents (9:1 DMSO:H2O, 4 mL) was prepared in a Pierce reaction vessel. L-proline (78 mg, 0.68 mmol), sodium carbonate (72 mg, 0.68 mmol), sodium azide (265 mg, 4.07 mmol), copper sulfate, pentahydrate (43 mg, 0.17 mmol), and sodium ascorbate (67 mg, 0.34 mmol), respectively, were then added to the vessel. The reaction vessel was capped and the mixture was heated at 65° C. for 18 hours. The reaction mass was poured into 50 mL of ice-water, stirred for 10 minutes, and extracted with ethyl acetate (3×30 mL). The combined organic extract was then washed with brine (50 mL), dried over Na2SO4, and evaporated under vacuum. The resulting crude compound was auto purified through preparative HPLC to yield the desired 1-(furan-2-yl)-4-phenyl-1H-1,2,3-triazole (36 mg, 5%) as a light yellow solid. The melting point of the final product was determined to be 99-101° C. The HPLC purity of the final product was 95.34%. LC-MS [M+1]212 (C12H9N3O+H expected 212.07). The 1H-NMR spectra was in accordance with the chemical structure.

Workup

  1. customwas prepared in a Pierce reaction vessel
  2. customThe reaction vessel was capped
  3. extractionextracted with ethyl acetate (3×30 mL)
  4. extractionThe combined organic extract
  5. washwas then washed with brine (50 mL)
  6. dry with materialdried over Na2SO4
  7. customevaporated under vacuum
  8. custompurified through preparative HPLC

Sources & evidence

ORD record
ord-b667a46d36ad4ebaa41f8740114c0994
Source dataset
uspto-grants-2016_08
Patent number
US09402397B2

Reaction notes

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