4-Toluenesulfonyl chloride → HCID 20510480, compound

Participants

Reaction Steps

N-Tosyloxytetrachlorophthalimide was prepared by the following procedure. To a flask equipped with a stirrer and addition funnel were added N-hydroxytetrachlorophthalimide (10.00 g, 0.033 mol), p-toluenesulfonyl chlorde (6.57 g, 0.033 mol) and 100 mL of dried tetrahydrofuran (THF). A solution of triethylamine (4.5 mL, 0.033 mol) in 20 mL of THF was added dropwise while the reaction vessel was cooled to between -20° and -10°. A red color formed after each drop, and quickly disappeared. After stirring for 2 h at room temperature the reaction mixture was diluted with 200 mL of methylene chloride, and the solution was washed twice with water. The organic layer containing much crystallized product was evaporated, leaving 13.5 g of pale yellow N-tosyloxytetrachlorophthalimide: mp 206°-210°. Recrystallization from toluene (50 mL)-heptane (25 mL) gave 10.7 g (71.5%) of pale yellow product: mp 214°-216°; ir (KBr) 1800 (w), 1740 (vs), 1380 (m), 1190 (m), 1180 (m), 1140 (m), 1025 (m), 810 (m), 790 (m), 725 (m), 705 (m), 506 (m); uv (CH3CN) 240 (58,500), 275 (2990), 328 (2790), 339 nm (3020); mass spectrum 452.8782 (calcd for C15H7NO5Cl4S: m+, 452.8805). Anal. Calcd for C15H7NO5Cl4S: C, 39.59; H, 1.55; N, 3.08; O, 17.58; Cl, 31.16; S, 70.4. Found: C, 40.04, 40.16, 39.70, 39.72; H, 1.95, 1.81, 1.52, 1.70; N, 2.99, 2.89; Cl, 31.30.

Provenance & Evidence