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insoluble polyurea (removed by filtration)

Procedure: Preparation of 45 [30]

The amides and sulfonamides were synthesized by treating N-benzylmethylamine 44 (0.302 g, 2.5 mmol) with an acid chloride or sulfonyl chloride (3.5 mmol) in DMF (2 mL) and triethylamine (5 mmol). The reaction mixture was stirred for 4 h and was then quenched with potassium sarcosinate (0.127 g, 1 mmol) and water (6 mL).The product 45 was isolated by filtration in the case of solids and extracted in ethyl acetate (10 mL) in the case of oils.The organic extract was pipetted out and evaporated to give the product.

Procedure: Preparation of 46 [31]

Procedure for the formation of amides 46 or sulfonamides using an acid chloride or sul-fonyl chloride respectively with an excess amine:To a solution of acid chloride or sulfonyl chloride (0.1 mmol) in dichloromethane (1 mL) was added a solution of the amine (3 equiv.) in dichloromethane (1 mL).The mixture was stirred at rt for 30 min and a solution of 1,4-phenylene diisocyanate (6 equiv.) in dichloromethane (4 mL) was added. The mixture was stirred at rt for 40 min and a solution of pentaethylenehexamine (2.5 equiv.) in dichloromethane (4 mL) was added. After stirring for 1 h, the heterogeneous mixture was filtered. Evaporation of the solvent under reduced pressure afforded the expected amide 46 or sulfonamide.

Procedure for the formation of amides 46 or sulfonamides using an amine with excess acid chloride or sulfonyl chloride respectively: To a solution of amine (0.1 mmol) in dichloromethane (1 mL) was added a solution of the acid chloride or sulfonyl chloride (3 equiv.) in dichloromethane (1 mL) and polyvinylpyridine (100 mg).The mixture was stirred at rt for 40 min and a solution of pentaethylenehexamine (3 equiv.) in dichloromethane (4 mL) was added.The mixture was stirred at rt for 40 min and a solution of 1,4-phenylene diisocyanate (3 equiv.) in dichloromethane (4 mL) was added. After stirring for 1 h, the heterogeneous mixture was filtered. Evaporation of the solvent under reduced pressure afforded the expected amide 46 or sulfonamide.

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