ChemicalBook CAS DataBase List Benzenesulfonyl hydrazide

Benzenesulfonyl hydrazide synthesis

5synthesis methods

Product Name:Benzenesulfonyl hydrazide
CAS Number:80-17-1
Molecular formula:C6H8N2O2S
Molecular Weight:172.2

Benzenesulfonyl hydrazides are produced by treating benzenesulfonyl chlorides with hydrazine in dioxane, alcohol, or water and in the presence of a second equivalent of hydrazineoranotherbase. They react with nitrous acid to form benzenesulfonyl azides according to the following equation:
ArSO₂NHNH₂ +HNO₂→RSO₂N₃ +2H₂O

98-09-9
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80-17-1
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Yield:80-17-1 90%

Reaction Conditions:

with hydrazine hydrate in tetrahydrofuran at -8; for 0.5 h;

Steps:

General Procedure for Sulfonylhydrazide Synthesis (2a-h)
General procedure: To a solution of 80% hydrazine hydrate (0.1 ml, 2.1 mmol, 2.1 eq) in THF (10 ml) was slowly added sulfonylchloride (1 mmol, 1 eq). The mixture was stirred at -8°C for 30 min. The mixture was extracted with ethyl acetate, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel 60 (Merck; CHCl₃/CH₃OH, 9.4:0.6) to give sulfonylhydrazides. Benzenesulfonohydrazide (2a) (yield, 90%) Melting point, 102-104°C. ¹H NMR (300 MHz, CDCl₃, δ= ppm): 3.62 (2H, s), 5.62 (1H, s), 7.57 (2H, t, J = 7.3 Hz), 7.65 (1H, t, J = 7.3 Hz), 7.93 (2H, d, J = 7.0 Hz). ¹³C NMR (75 MHz, CDCl₃, δ = ppm): 128.2, 129.3, 133.5, 136.3.

References:

Fernandes, Thais Batista;de Azevedo, Ricardo Alexandre;Yang, Rosania;Teixeira, Sarah Fernandes;Trossini, Gustavo Henrique Goulart;Barbuto, José Alexandre Marzag?o;Ferreira, Adilson Kleber;Parise-Filho, Roberto [Letters in drug design and discovery,2018,vol. 15,# 12,p. 1288 - 1298]

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