ChemicalBook CAS DataBase List Benzenesulfonamide, N-(4-hydroxyphenyl)-

Benzenesulfonamide, N-(4-hydroxyphenyl)- synthesis

7synthesis methods

Product Name:Benzenesulfonamide, N-(4-hydroxyphenyl)-
CAS Number:5471-90-9
Molecular formula:C12H11NO3S
Molecular Weight:249.29

123-30-8 Synthesis

123-30-8
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$10.00/5g

98-09-9
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$12.00/25g

Benzenesulfonamide, N-(4-hydroxyphenyl)-

5471-90-9
35 suppliers
$50.00/250mg

Yield:5471-90-9 77%

Reaction Conditions:

with pyridine in N,N-dimethyl-formamide at 0 - 20;Inert atmosphere;

Steps:

4.2.1. General procedure 1. Sulfonylation of para-aminophenol: preparation of N-(4-hydroxyphenyl)-benzenesulfonamide 8a (R⁴=SO₂Ph)

General procedure: To a cooled (0 °C) solution of para-aminophenol (10,9 g, 100 mmol) in DMF (20 mL) was added pyridine (20 mL) and then dropwise (over a 10 min period) benzenesulfonyl chloride (12,8 mL, 100 mmol). The mixture was allowed to warm to rt and was stirred for one additional hour. After this time, water (150 mL) and EtOAc (100 mL) were added. After decantation, the aqueous phase was extracted with EtOAc (100 mL). The combined organic phases were washed with water (150 mL), 5% w/w aqueous solution of copper sulfate (150 mL) and brine (150 mL), dried over Na₂SO₄ and filtered. After removal of the solvent under reduced pressure, the crude product was purified by flash chromatography (cyclohexane/EtOAc 60:40) to afford compound 8a (19.22 g, 77%) as a white solid; mp 160 °C (lit.¹³ 156 °C). ¹H NMR (300 MHz, DMSO-d₆): δ=6.59 (2H, d, J=9.0, ArH), 6.82 (2H, d, J=9.0, ArH), 7.51 (2H, m, SO₂(m-ArH)), 7.59 (1H, m, SO₂(p-ArH)), 7.63-7.67 (2H, m, SO₂(o-ArH)), 9.31 (1H, very br s, NHSO₂Ph or OH), 9.71 (1H, very br s, OH or NHSO₂Ph).

References:

Baragona, Fabien;Lomberget, Thierry;Duchamp, Christian;Henriques, Natali;Lo Piccolo, Eugenio;Diana, Patrizia;Montalbano, Alessandra;Barret, Roland [Tetrahedron,2011,vol. 67,# 45,p. 8731 - 8739] Location in patent:experimental part