Chloramine

N-Amination of Pyrrole and Indole Heterocycles with Monochloramine (NH2Cl)

“…Preparation of Anhydrous Ethereal Monochloramine. NH 4 Cl (3 g, 56 mmol) in ether (110 mL) was cooled to −5 °C, and concentrated NH 4 OH (4.7 mL) was added via pipet. Commercial bleach (Clorox, 72 mL) was then added via addition funnel over 15 min.…”

“…This oxidation product was observed by LCMS. Interestingly, amines and alcohols can be oxidized upon prolonged exposure to NH 2 Cl: 2PhNH 2 + 2NH 2 Cl → PhNNPh + 2NH 4 Cl; see ref a.…”

“…To our knowledge, this represents the first application of NH 2 Cl for aromatic heterocycle N-aminations. Ethereal NH 2 Cl is readily prepared from NH 4 Cl, NH 4 OH, and bleach, and the reaction byproducts are enviromentally benign. Furthermore, this transformation is highly efficient: 31% of the reagent is consumed in the reaction as compared to 8.1% for 1 .…”

A Convenient Reductive Deamination (Hydrodeamination) of Aromatic Amines

“…Note: Although no problems were experienced in the preparation and handling of chloroamine using this procedure, it should be noted that only dilute solutions of chloroamine should be prepared. More concentrated solutions readily decompose potentially creating a safety hazard . The preparation and reactions of chloroamine should also be carried out in a well-ventilated hood.…”