Diethyl Ether → O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

Participants

Reaction Conditions

Reaction Steps

(Adapted from: Miki, Y. et. al.; Heterocycles 1996, 43, 2249-2256; 2-[(aminooxy)sulfonyl]-1,3,5-trimethylbenzene was prepared using the procedure described in Krause, J. G. Synthesis, 1972, 3, 140). A solution of 3-bromo-5-methoxypyridine (8.72 g, 46.4 mmol) in dichloromethane (93 ml) was cooled to 0° C. A solution of 2-[(aminooxy)sulfonyl]-1,3,5-trimethylbenzene (13.31 g, 46.4 mmol) in dichloromethane (93 ml) was added in a steady stream via canula and the mixture was allowed to stir for 1 h at 0° C. At this time, 460 mL of ether was added dropwise via addition funnel over 5 minutes. The precipitated solid was collected via filtration, and washed with cold ether. The solid was placed under vacuum for 30 minutes to afford 1-amino-3-bromo-5-methoxypyridinium 2,4,6-trimethylbenzenesulfonate as a colorless solid.

Provenance & Evidence