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ChemicalBook CAS DataBase List 6-Nitro-1,2-benzisothiazolin-3-one 1,1-dioxide

6-Nitro-1,2-benzisothiazolin-3-one 1,1-dioxide synthesis

13synthesis methods
6269-91-6 Synthesis
2-Methyl-5-nitrobenzenesulfonamide

6269-91-6
140 suppliers
$9.00/5g

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Yield: 72%

Reaction Conditions:

with chromium(VI) oxide;sulfuric acid in water at 20; for 24 h;

Steps:

4.2.3. 6-Nitrosaccharin (4)
To solution chromium trioxide (20.4 g, 0.204 mol) in water (150 mL) was added concentrated sulfuric acid (190 mL) dropwise in the ice bath. 2-Methyl-5-nitrobenzenesulfonamide (10 g, 46.3 mmol) was added and the mixture was stirred at room temperature for 24 h. The mixture was filtered and the residue washed with water, dissolved in sodium bicarbonate solution and filtered under vacuum. The filtrate was acidified with concentrated HCl. After the precipitated product was filtered and washed with abundant cold water, it was dried in the vacuum-oven at 40 °C. The product was obtained a white powder in 72% yield. Mp 205.6-205.8 °C, (lit.36 205-207 °C); IR: 3103, 1720, 1608, 1541, 1354, 1340, 1184, 1128 cm-1; 1H NMR (DMSO-d6, 300 MHz) δ/ppm: 8.02 (1H, d, J = 8.5 Hz), 8.56 (1H, d, J = 8.2 Hz), 8.71 (1H, s), 10.2 (1H, br, NH); 13C NMR (DMSO-d6, 75 MHz) δ/ppm: 117.2, 126.4, 129.8, 135.2, 143.0, 151.7, 162.2.

References:

Gener, Nahit;Demir, Dudu;Sonmez, Fatih;Kucukislamoglu, Mustafa [Bioorganic and Medicinal Chemistry,2012,vol. 20,# 9,p. 2811 - 2821] Location in patent:experimental part

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