ChemicalBook CAS DataBase List Benzenesulfonylazide

Benzenesulfonylazide synthesis

10synthesis methods

Product Name:Benzenesulfonylazide
CAS Number:938-10-3
Molecular formula:C6H5N3O2S
Molecular Weight:183.1878

Benzenesulfonylazide is prepared by the reaction of Benzenesulfonyl Chloride with excess Sodium Azide in a water-ethanol mixture. The formation of ethyl benzenesulfonate as a byproduct may be avoided by addition of neat benzenesulfonyl chloride to an ethanolic solution of sodium azide. A preparation of benzenesulfonyl azide by oxidation of phenylsulfonylhydrazine in the presence of clay-supported iron(III) nitrate (clayfen) has been reported.

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Yield: 98%

Reaction Conditions:

Stage #1:benzenesulfonic acid with trichloroisocyanuric acid;triphenylphosphine in tetrahydrofuran at 0 - 5;
Stage #2: with sodium azide in tetrahydrofuran at 5 - 20;

Steps:

General procedure: 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. p-Toluenesulfonyl azide was obtained with 98% yield after removing the solvent under reduced pressure.

References:

Kiani, Adeleh;Akhlaghinia, Batool;Rouhi-Saadabad, Hamed;Bakavoli, Mehdi [Journal of Sulfur Chemistry,2014,vol. 35,# 2,p. 119 - 127]