Non-templated syntheses

In 1954, Stetter and Roos7 reported that the condensation of terminal halides with bis-sulfonamide sodium salts proceeded under conditions of high dilu- 

Caution Carry out all procedures in a well-ventilated hood, and wear disposable vinyl or latex gloves and chemical-resistant safety goggles. 

The following procedure is representative of a co-cyclisation of a bis-toluenesulfonamide with a bis-toluenesulfonate followed by tosyl deprotection with sulfuric acid. 

Charge a double-necked round-bottomed flask (1 L) with potassium carbonate (14.6 g, 308 mmol), triethylenetetramine (10 g, 68.4 mmol) and water (400 mL), and add a large Teflon-coated magnetic stirrer bar. Place the flask in an oil bath, attach a water-cooled condenser and heat to 80°C, while stirring the mixture vigorously. 

Add p-toluenesulfonyl chloride (57.5 g, 302 mmol) in small portions as a solid over a period of 3 h. Heat and stir the mixture overnight, and then allow the mixture to cool when a colourless precipitate is evident. Filter the solid on a sintered filter funnel, and wash the solids in turn with water (3 x 50 mL), methanol (3 x 50 mL) and finally diethyl ether (3 x 50 mL). Dry the solid under high vacuum ( 0.1 mmHg, 60°C) to yield the acyclic tetra-tosylamide (44.8 g, 86%), m.p. 211-212°C. 

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