Hydrochloric Acid → N,N'-ethane-1,2-diylbis[4-methyl-N-(2-{[(4-methylphenyl)sulfonyl]amino}ethyl)benzenesulfonamide]

Participants

Reaction Steps

Procedure 3 is further illustrated by the preparation of racemic 6e'. A solution of 80 g of p-tosyl chloride in 300 ml. of dry pyridine was cooled to 0° and added to a cooled, stirred solution of triethylenetetramine (MCB, technical) in 50 ml. of dry pyridine over a period of 3 hr. The solution was kept at 0° during addition. The solution was allowed to stand at 0° for 24 hrs, and mixed with 100 ml. of concentrated hydrochloric acid and 1 kg. of crushed ice. The resulting aqueous solution was decanted, and the oily residue was triturated with methanol, filtered, and recrystallized twice from 50 ml. of dimethyl formamide and 300 ml. of 95% ethanol to give N,N',N",N'"-tetratosyltriethylenetetramine, 28.8 g. (38%), m.p. 211°-213°. The analytical sample was dried at 180° for 14 hrs at 10μ.

Provenance & Evidence