[OH-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([C:11]2[N:15]([NH2:16])[C:14]([CH3:18])([CH3:17])[O:13][N:12]=2)[CH:7]=[C:8]([CH3:10])[CH:9]=1.[CH2:19]([C:21]1[C:29]([O:30][CH3:31])=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24])[CH3:20].O>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:3][C:4]1[CH:5]=[C:6]([C:11]2[N:15]([NH:16][C:23](=[O:24])[C:22]3[CH:26]=[CH:27][CH:28]=[C:29]([O:30][CH3:31])[C:21]=3[CH2:19][CH3:20])[C:14]([CH3:18])([CH3:17])[O:13][N:12]=2)[CH:7]=[C:8]([CH3:10])[CH:9]=1
A 5% aqueous solution of NaOH (4 mL) was added to a solution of 3-(3,5-dimethyl-phenyl)-5,5-dimethyl-[1,2,4]oxadiazol-4-ylamine (90 mg) in 6 mL of toluene. 2-Ethyl-3-methoxybenzoyl chloride (140 mg) was then added to the mixture. The reaction was stirred at room temperature for 30 hours. Water and CHCl3 were added. The organic phase was separated, dried over MgSO4, and the solvent was removed in vacuo. The residue was triturated with 100 mL of 10% ether in hexane by magnetic stirring of the mixture in a vessel for 1 hour. Filtration and air-drying of the resultant solid provided 62 mg (40% yield) of N-[3-(3,5-dimethyl-phenyl)-5,5-dimethyl-[1,2,4]oxadiazol-4-yl]-2-ethyl-3-methoxy-benzamide. 1H-NMR (300 MHz, CDCl3) δ (ppm): 7.42 (s, 2H), 7.11 (s, 1H), 7.11 (t, 1H), 6.9 (d, 1H), 6.67 (d, 1H), 3.81 (s, 3H), 2.55 (q, 2H), 2.34 (s, 6H), 1.7 (br s, 6H), 1.05 (t, 3H), Rf=0.5 (1:1 ethyl acetate:hexane). The filtrate contained an additional quantity of the intended product.
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