4-Acetamidobenzenesulfonyl azide

4-Acetamidobenzenesulfonyl azide is an important organic intermediate (building block) to synthetize substituted amidobenzene products.

4-Acetamidobenzenesulfonyl azide is used as a hydroazidation catalyst for facile preparation of organoazides. It is used as a reagent for synthesis of: monosaccharide-derived alcohols, a late-stage intermolecular C-H olefination, intramolecular isomuenchnone cycloaddition approach to antitumor agents, rhodium-catalyzed carbene cyclization cycloaddition cascade reaction of vinylsulfonates and Suzuki-Miyaura cross coupling reaction.

Hydroazidation Catalyst for Facile Preparation of Organoazides

Diazo transfer agent.

reaction type: click chemistry

To a solution of CCA(0.1548 g, 0.6 mmol) in tetrahydrofuran (3-5 mL), PPh3 (0.5246 g, 2 mmol)was added at 0-5°C with stirring. A white suspension was formed to which p-toluenesulfonic acid (0.1720 g, 1 mmol) was added and stirring continued for 15 min. NaN3 (0.065 g, 1 mmol) was added and the temperature was raised up to room temperature. Stirring was continued for 1 min at room temperature. After completion of the reaction (TLC), the reaction mixture was concentrated, washed with EtOAc (4-6 mL), and cold distilled water (5 mL). The organic layer was dried with anhydrous Na2SO4, passed through a short silica-gel column using n-hexane/ethylacetate (10/1) as eluent. 4-Acetamidobenzenesulfonyl azide was obtained after removing the solvent under reduced pressure.

Under ambient conditions, 4-acetamidobenzenesulfonyl azide (4-ABSA) belongs to a monoclinic structure with a P21 space group and cell parameters of a = 8.0529 Å, b = 22.988 Å, c = 8.3123 Å, β=93.534°, respectively. The hydrogen-bonding interactions allow molecules to pair up and form π-stacked dimers. The studies of NH4N3 have reported that the hydrogen bonds are affected by the rotation of azide ions with increasing pressure. The cooperativity of hydrogen bonds and π-stacking interactions allow 4-ABSA to become an attractive candidate for studying the influence of non-covalent interactions within the organic azides in the compression process. In addition, the bent azide groups of 4-ABSA are crucial for electron orbit hybridization and nitrogen polymerization.

[1] Junru Jiang. “High-Pressure Studies of 4-Acetamidobenzenesulfonyl Azide: Combined Raman Scattering, IR Absorption, and Synchrotron X-ray Diffraction Measurements.” The Journal of Physical Chemistry B 120 46 (2016): 12015–12022.