[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]
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.
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