4-Toluenesulfonyl chloride → HCID 10857214, compound

Participants

Reaction Conditions

Reaction Steps

To 62.9 parts of (S)-1,2-propanediamine under a nitrogen atmosphere (temp. 0°-5° C.) was added dropwise over 7 hours a solution of 80.84 parts of 4-methylbenzenesulfonyl chloride in 1689 parts of dichloromethane. After stirring overnight at 20° C., the reaction mixture was washed with 250 parts of water (3x). The organic layer was separated dried, filtered and evaporated. About 1 gram of the thus obtained product was dissolved in 4-methyl-2-pentanol by heating just below the reflux temperature. The mixture was allowed to cool slowly and at about 30° C. was seeded with the previously obtained crystals. After further cooling to 0° C., the precipitate was filtered off and triturated with 2,2'-oxybispropane. The crystals were filtered off, dried in vacuo, yielding 50.75 parts (52.4%) of (S)-N-2-aminopropyl-4-methylbenzenesulfonamide; mp. 82°-86° C.; [α]D20 =-1.10° (c=1% in methanol) (interm.1).

Provenance & Evidence