[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]#[N:6].C(=O)([O-])[O-].[K+].[K+].[Cl:24][CH2:25][C:26](Cl)=[O:27].Cl>CC(C)=O>[Cl:24][CH2:25][C:26]([NH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]#[N:6])=[O:27]A slurry of 3-amino-4-(benzyloxy)benzonitrile (7 g, 31.2 mmol) and anhydrous potassium carbonate (8.6 g, 62.4 mmol) in 50 mL of acetone was stirred under nitrogen as chloroacetylchloride (2.6 mL, 33 mmol) was added portion-wise. The reaction was stirred overnight. The reaction was poured into ice water and the liquid was neutralized with 6 N hydrochloric acid. The resulting solid was isolated by filtration, washed with water, and dried under reduced pressure to give 3-((chloromethyl)carbonylamino)-4-(benzyloxy)benzonitrile (8.3 g) as a white solid; NMR (CDCl3, TMS) δ4.22 (s, 2), 5.23 (s, 2), 7.03 (d, 1), 7.43 (m, 7), 8.73 (d, 1).
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