O-TOLYL-METHANESULFONYL CHLORIDE synthesis

Yield:-

Reaction Conditions:

with hydrogenchloride;N-chloro-succinimide in water;acetonitrile at 0 - 20; for 0.5 h;

Steps:

4.1.3. General procedure for preparation of sulfonyl azides 24a-k

General procedure: Various alkyl halides 23a-k (2.5 mmol) and thiourea (0.19 g, 2.5 mmol) were refluxed together in EtOH (2.5 mL) for 1 h. Afterr emoval of EtOH at reduced pressure, the obtained solid was slowly added to a mixture of NCS (1.33 g, 10 mmol), 2 M HCl (0.68 mL) and MeCN (4 mL) over 15 min. Upon completion of the reaction (TLC monitoring), the solvent was removed under vacuum. Then H₂O(5 mL)was added to the residue and stirred for 15 min, the resulting solid was filtered and dried under an infrared lamp to afford the corresponding sulfonyl chlorides 24a-k. Without further purification, 24a-k was added in portions to a solution of NaN₃ (195 mg ,3 mmol) in acetone/H2O (10 mL, acetone/H₂O = 1:1) at 0 °C. After being stirred at room temperature for 4 h, the reaction mixtur ewas concentrated in vacuo and H₂O (10 mL) was added to the residue. The aqueous solution was extracted with CHCl3 (3 x 10 mL). The combined organic layers were washed with brine, dried over Na₂SO₄, filtered and concentrated under reduced pressure to afford sulfonyl azides 25a-k.

References:

Fang, Sen-Biao;Li, Hui-Jing;Nan, Xiang;Wu, Rui;Wu, Yan-Chao;Zhang, Jing;Zhang, Zhi-Zhou [European Journal of Medicinal Chemistry,2020,vol. 200]