C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[S:12][C:11]([C:13]([OH:15])=O)=[CH:10][CH:9]=1.[CH3:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([NH2:25])[CH:20]=1)=[O:18].C(N(CC)CC)C>C(Cl)Cl.C(OCC)(=O)C.CN(C=O)C>[C:17]([C:19]1[CH:20]=[C:21]([NH:25][C:13]([C:11]2[S:12][C:8]([Cl:7])=[CH:9][CH:10]=2)=[O:15])[CH:22]=[CH:23][CH:24]=1)(=[O:18])[CH3:16]Oxalyl chloride (4.9 mL, 56.00 mmol) was added to solution of 5-chloro-thiophene-2-carboxylic acid (4.78 g, 29.40 mmol), DMF (0.25 mL), and CH2Cl2 (50 ml) at room temperature. After stirring overnight, the reaction was stripped of solvent and unreacted oxalyl choride in vacuo, giving a colorless oil. The oil was dissolved in CH2Cl2 (50 mL), and treated with 3-aminoacetophenone (3.78 g, 28.00 mmol) and triethylamine (4.68 mL, 33.60 mmol). After stirring for 1 h, the mixture was diluted with 800 mL of ethyl acetate, extracted with 1N HCl, 1N NaHCO3, brine, and dried over MgSO4. The resulting solution was concentrated in vacuo to a volume of 100 mL, giving 5-chloro-thiophene-2-carboxylic acid (3-acetyl-phenyl)-amide as a white powder, which was collected by filtration and dried under high vacuum (8.12 g, 81% yield).
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