[CH3:1][C:2]1([CH3:14])[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:3]1[NH2:13].C([C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1)C.[OH-].[Na+].[CH2:28](O)[CH3:29]>O>[CH3:1][C:2]1([CH3:14])[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:3]1[NH:13][C:21](=[O:22])[C:20]1[CH:19]=[CH:18][CH:17]=[C:25]([CH2:28][CH3:29])[CH:24]=1To an ice-cold stirred solution of the 5,5-dimethyl-3-phenyl-[1,2,4]oxadiazol-4-ylamine (0.5 g, 2.6 mmol) in 6 mL of ethanol, was added an excess of 4-ethylbenzoyl chloride (4 mL), followed by aqueous NaOH (8%, 7 mL). The solution was stirred overnight and allowed to warm to room temperature. The mixture was diluted with water and extracted with CH2Cl2. The combined CH2Cl2 extracts were dried over MgSO4, and the solvent was removed in vacuo. The product, N-(5,5-dimethyl-3-phenyl-[1,2,4]oxadiazol-4-yl)-3-ethyl-benzamide, was isolated by silica gel chromatography. 1H-NMR (300 MHz, CDCl3) δ (ppm): 7.8 (m, 3H), 7.6 (d, 2H), 7.4 (m, 2H), 7.2 (d, 2H), 2.7 (q, 2H), 1.65 (s, 6H), 1.2 (t, 3H).
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