[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH2:13][C:14]2[O:15][CH:16]=[CH:17][CH:18]=2)[C:11]#[N:12])=[CH:6][CH:5]=1.CN(C=O)C.Cl.Cl[CH2:26][N:27]1[CH:31]=[N:30][CH:29]=[N:28]1>CCCCCC.C(OCC)(=O)C.CCOCC.O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:11]#[N:12])([CH2:13][C:14]2[O:15][CH:16]=[CH:17][CH:18]=2)[CH2:26][N:27]2[CH:31]=[N:30][CH:29]=[N:28]2)=[CH:6][CH:5]=1
To a flask under a nitrogen atmosphere was added 1.66 g. (0.069 mole) of 60% sodium hydride, which had been washed twice with hexane to remove the mineral oil, in 40 ml. of dry DMF. To this slurry at room temperature was added with stirring 6.40 g. (27.7 mmoles) of 2-(4-chlorophenyl)-3-(2-furyl)propionitrile in 25 ml. of dry DMF. The mixture was stirred for 45 minutes and then 4.66 g. (30.47 mmoles) of 1-(chloromethyl)-1,2,4-triazole hydrochloride was added directly in two portions. The flask contents were stirred for six hours after which 1.6 g. of 60% sodium hydride which had been washed with hexane to remove the oil was added to complete the reaction. Water, 20 ml., was added dropwise followed by 100 ml. of ether and 50 ml. of ethyl acetate. The combined extracts were dried, decolorized with activated charcoal, filtered through infusorial earth, and concentrated to give a thick oil which crystallized on cooling to 3.2 g. (37.1% yield) of 1-[2-(4-chlorophenyl)-2-cyano-3-(2-furyl)propyl]-1,2,4-triazole as a light yellow solid, melting point 112°-114° C.
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