P-Toluenesulfonamide → 5-Chloro-2-tosylisoindoline

Participants

Reaction Steps

To a suspension of 60% sodium hydride (3 gr, 0.125 mmol) in mineral oil in 80 ml of anhydrous DMF (100 ml) was dropwise added a solution of para-toluen sulphonamide (5.6 gr, 32.60 mmol) in 30 ml of DMF over 1 hour under vigorous stirring at room temperature. After the addition, the mixture was stirred for 1 hour at room temperature and another 1 hour heating at 90° C. To this mixture was added dropwise a solution of 1,2-Bis-bromomethyl-4-chloro-benzene (4 g, 14.18 mmol) in 20 ml of anhydrous DMF at 60° C. and overnight at room temperature. The resultant mixture was poured over ice and the resulting precipitates were collected by filtration. The precipitates were washed with 1N hydrochloric acid, 5% sodium carbonate and brine. Concentration gave 2.8 gr of 5-Chloro-2-(toluene-4-sulfonyl)-2,3-dihydro-1H-isoindole as a pale yellow solid. MS: [M+H]+ 308

Provenance & Evidence