ChemicalBook CAS DataBase List 3-(METHYLSULFONYL)ANILINE

3-(METHYLSULFONYL)ANILINE synthesis

9synthesis methods

Product Name:3-(METHYLSULFONYL)ANILINE
CAS Number:35216-39-8
Molecular formula:C7H9NO2S
Molecular Weight:171.22

1783-81-9
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35216-39-8
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Yield: 92%

Reaction Conditions:

with sodium tungstate;dihydrogen peroxide;acetic acid in water at 65; for 1.5 h;

Steps:

E Oxidation of methylthio aniline to methylsulfonyl aniline
General procedure: A mixture of Na₂W0₄ (0.067 g), 1 drop of acetic acid, and H₂0 (5 mL) was placed in a flask and heated to 65 °C. Methylthioaniline 153, 154, or 161 (500 mg, 3.59 mmol) was added, followed by dropwise addition of H₂0₂ (1.1 mL, 10.77 mmol). The mixture was stirred at 65 °C for 1.5 h and, after cooling, 80 mL of 1 N HC1 and 50 mL of DCM were added. The layers were separated, and the aqueous phase was washed with additional DCM. The aqueous phase was basified with 25% NaOH and extracted with DCM. The organic phase was washed with brine and dried over Na₂S0₄. The solvent was removed to give methylsulfonyl aniline derivatives 157, 158 and 164. [0232] 3-(methylsulfonyl)aniline (158). Compound 158 was prepared according to procedure E from 153 to afford 557 mg of brown powder (92%). 1H NMR (500 MHz, CDC1₃) δ 3.03 (s, 3H), 6.89 (ddd, J = 0.8, 2.3, 8.0 Hz, 1H), 7.21 (t, J = 2.1Hz, 1H), 7.24 (dt, J = 1.1, 7.7Hz, 1H), 7.30 (t, 7.8Hz, 1H). ¹³C NMR (126 MHz, CDC1₃) δ 44.40, 112.69, 116.37, 119.72, 130.30, 141.16, 147.69. LCQ (M+H⁺) calcd C7H₉N0₂S 172, found 172.