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Volumn 36, Issue 12, 2007, Pages 1456-1457

Highly efficient method for the synthesis of carboxamides from carboxylic acids and amines using benzenesulfonic anhydride (BSA)

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EID: 38149118837     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2007.1456     Document Type: Article
Times cited : (4)

References (34)
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    • Typical experimental procedure for the preparation of 3-phenyl-N-(3-phenylpropyl)propanamide is shown in the following: To a stirred solution of 3-phenylpropionic acid (49.6 mg, 0.33 mmol) in CH2Cl 2 (1.5 mL) were successively added benzenesulfonic anhydride (107.5mg, 0.36mmol) and DMAP (88.1 mg, 0.72 mmol) at room temperature. After having been stirred for 10 min, a solution of 3-phenylpropylamine (40.6 mg, 0.30 mmol) in CH2Cl2 (1.5 mL) was added. After the reaction mixture was stirred for 1h, it was quenched with saturated aqueous sodium hydrogencarbonate. The mixture was extracted with EtOAc. The organic layer was washed with saturated aqueous sodium hydrogencarbonate, brine, dried over anhydrous Na2SO4, and evaporated. The crude product was purified by preparative TLC (hexane/EtOAc, 1/9) to afford 3-phenyl-N-(3- phenylpropyl)propanamide 79.8 mg, quant, as a white solid
    • 4, and evaporated. The crude product was purified by preparative TLC (hexane/EtOAc = 1/9) to afford 3-phenyl-N-(3- phenylpropyl)propanamide (79.8 mg, quant.) as a white solid.


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