Methyl Ethyl Ketone → HCID 19099687, compound

HRID 1975325Notes

Reaction equation

HRID 1975325 reaction equation
[C:1]([C:5]1[N:9]=[C:8]([OH:10])[N:7]([C:11](=[O:14])[NH:12][CH3:13])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].CC(CC)=O.[CH2:26](Cl)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O>[CH2:26]([O:10][C:8]1[N:7]([C:11](=[O:14])[NH:12][CH3:13])[N:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[N:9]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 178485827HCID 178485827, compound

Product 1

HCID 19099687HCID 19099687, compoundYield 3.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 3-tert-butyl-1-N-methylcarbamoyl-5-hydroxy-1,2,4-triazole 5.94 g (0.03 mole) and potassium carbonate 6.21 g (0.045 mole) was added 100 ml of methyl-ethyl ketone. Then to the mixture was added, while stirring, 4.17 g (0.033 mole) of benzyl chloride, and the mixture was heated under reflux for 2 hours. After the reaction mixture was concentrated under a reduced pressure, the residue obtained was diluted with water and extracted with methylene chloride. The organic phase was dried over anhydrous sodium sulfate, and then concentrated under a reduced pressure, and the pale yellow oily substance obtained was subjected to silica gel column chromatography and eluted with a solvent mixture of 1:2 of ethyl acetate and n-hexane, to give 0.3 g of 5-benzyloxy-3-tert-butyl-1-N-methylcarbamoyl- 1,2,4-triazole as a white solid (yield 3.5%).

Workup

  1. additionThen to the mixture was added
  2. temperatureunder reflux for 2 hours
  3. concentrationAfter the reaction mixture was concentrated under a reduced pressure
  4. customthe residue obtained
  5. extractionextracted with methylene chloride
  6. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under a reduced pressure
  8. customthe pale yellow oily substance obtained
  9. washeluted with a solvent mixture of 1:2 of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-977788367dd0412080c9072013037a59
Source dataset
uspto-grants-1994_02
Patent number
US05286738

Reaction notes

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