Propargyl bromide → 2-(1,1-Dimethylethyl)-2,4-dihydro-5-phenyl-4-(2-propyn-1-yl)-3H-1,2,4-triazol-3-one

HRID 892699Notes

Reaction equation

HRID 892699 reaction equation
[C:1]([N:5]1[C:9](=[O:10])[N:8]=[C:7]([C:11]2[CH:16]=[CH:15][CH2:14][CH2:13][CH:12]=2)[NH:6]1)([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C.C(=O)([O-])[O-].[K+].[K+].[CH2:29](Br)[C:30]#[CH:31]>C1(C)C=CC=CC=1.O>[C:1]([N:5]1[C:9](=[O:10])[N:8]([CH2:31][C:30]#[CH:29])[C:7]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 7842Propargyl bromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 178448764HCID 178448764, compound

Product 1

HCID 190109342-(1,1-Dimethylethyl)-2,4-dihydro-5-phenyl-4-(2-propyn-1-yl)-3H-1,2,4-triazol-3-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of crude 345 g (1.2 mol) of 1-t-butyl-4-H-3-phenyl-1,2,4-triazol-5-one and 3.5 L of ethyl acetate containing 0.03% water was stirred at room temperature and 190 g (1.67 mol) of solid potassium carbonate (K2CO3) was added. The mixture was heated at reflux for 0.5 h and 248 g (1.67 mol) of an 80% weight solution of propargyl bromide in toluene was added dropwise over 30 minutes. Refluxing was continued for an additional 3 h. The mixture was allowed to cool to room temperature, diluted with 2 L of water and stirred for 15 min. The organic layer was separated, washed with brine and dried over magnesium sulfate (MgSO4). Removal of the solvent left 300 g of an oil which was crystallized from 500 mL of ether and 1500 mL of hexanes to furnish 180 g of the desired compound, mp 82°-83° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 0.5 h
  3. temperatureRefluxing
  4. temperatureto cool to room temperature
  5. stirringstirred for 15 min
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried over magnesium sulfate (MgSO4)
  9. customRemoval of the solvent
  10. waitleft 300 g of an oil which
  11. customwas crystallized from 500 mL of ether and 1500 mL of hexanes

Sources & evidence

ORD record
ord-4b75f26b13bf4444b823f3624750d2d0
Source dataset
uspto-grants-1992_06
Patent number
US05120347

Reaction notes

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