Propylene Oxide → HCID 131722189, compound

HRID 1859017Notes

Reaction equation

HRID 1859017 reaction equation
[N:1]1[N:2]=[N:3][C:4](=[O:6])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[O:13]1[CH:15]([CH3:16])[CH2:14]1>CN(C=O)C>[OH:13][CH2:14][CH2:15][CH2:16][C:5]1[C:4](=[O:6])[N:3]=[N:2][N:1]=1

Participants

5

Reactant 3

HCID 6378Propylene OxideHCID 11430Potassium CarbonateHCID 22065216HCID 22065216, compound

Product 1

HCID 131722189HCID 131722189, compoundYield 283.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of triazolone 35 (248 mg, 0.5 mmol) and potassium carbonate (138 mg, 1 mmol) in DMF (6 ml), 1,2-epoxypropane (870 mg, 15 mmol) was added. The reaction mixture was heated at 60° C. for 18 h and concentrated in vacuo. The residue was treated with crushed ice, extracted with ethyl acetate (3×30 ml). The combined extract was washed with brine, dried (Na2SO4) and the solvent was removed under reduced pressure. The resulting crude product was purified on a column of silica gel (EtOAc/MeOH, 9:1) to give the hydoxypropyltriazolone 42 as a colorless solid (200 mg, 72%).

Workup

  1. additionwas added
  2. concentrationconcentrated in vacuo
  3. additionThe residue was treated with crushed ice
  4. extractionextracted with ethyl acetate (3×30 ml)
  5. extractionThe combined extract
  6. washwas washed with brine
  7. dry with materialdried (Na2SO4)
  8. customthe solvent was removed under reduced pressure
  9. customThe resulting crude product was purified on a column of silica gel (EtOAc/MeOH, 9:1)

Sources & evidence

ORD record
ord-579d33c761b34178bebb839df66b095e
Source dataset
uspto-grants-2000_11
Patent number
US06153616

Reaction notes

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