Triethylamine → O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

Participants

Reaction Steps

To a suspension of ethyl N-hydroxyacetimidate (4.72 g, 45.7 mmol) in DMF (453 ml) was added triethylamine (9.53 ml, 68.6 mmol) followed by portionwise addition of mesitylenesulfonyl chloride (1, 10 g, 45.7 mmol). The reaction mixture was stirred for 2 hours at room temperature then poured into ice water (150 mL). The resulting precipitate was collected by vacuum filtration. The collected solids were treated with neat perchloric acid (32.8 ml, 229 mmol) and stirred until homogeneous. Distilled water (30 mL) was used to titurate white crystals of O-mesitylenesulfonylhydroxylamine (2, 8.31 g, 38.6 mmol, 84% yield). MS APCI: [M+H]+ m/z 216.3.

Provenance & Evidence