[NH2:1][N:2]1[CH:6]=[N:5][CH:4]=[N:3]1.[F:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1>O1CCCC1.C(OCC)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>[F:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[N:1][N:2]2[CH:6]=[N:5][CH:4]=[N:3]2)=[CH:10][CH:9]=1A solution of 42.3 g (0.377 mol) of 75% pure 1-amino-1H-1,2,4-triazole, 40.0 mL (0.372 mol) of 4-fluorobenzaldehyde and 2.0 g of p-toluenesulfonic acid in 600 mL of tetrahydrofuran was stirred at room temperature for 21/2 days. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous Na2CO3, water and brine and dried (MgSO4). Removal of solvent gave a white solid which was recrystallized from n-butylchloride to afford 48.3 g (67%) of desired product as white needles; mp 118°-120° C. Concentration of the filtrate and recrystallization of the residue afforded 12.8 g (18%) more of product; mp 118°-120° C.
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