Preparation method of 4-(2-oxo-1-pyrrolinyl)benzenesulfonyl chloride_Kain Industrial Additive

Background and overview^[1]

4-(2-Oxo-1-pyrrolinyl)benzenesulfonyl chloride can be used as a pharmaceutical synthesis intermediate. If 4-(2-oxo-1-pyrrolinyl)benzenesulfonyl chloride is inhaled, move the patient to fresh air; if skin contact occurs, remove contaminated clothing and rinse skin thoroughly with soap and water, if necessary If you feel unwell, seek medical attention.

Preparation^[1]

The preparation method of 4-(2-oxo-1-pyrrolinyl)benzenesulfonyl chloride is as follows:

Method 1: Add 2 grams of phenylpyrrolidone to 20 ml of chlorosulfonic acid. The mixture was stirred at room temperature overnight. Stop the mixture by slowly adding ice. The aqueous mixture was extracted with 4 volumes of dichloromethane. The organic layers were combined, dried over Na2SO4 and concentrated in vacuo to obtain 4-(2-oxo-1-pyrrolinyl)benzenesulfonyl chloride as an off-white solid. Sulfonyl chloride was used without further purification (88% yield). 1HNMR (CDCl3): 2.19–2.30 (m, 2H), 2.69 (t, J=8.0Hz, 2H), 3.93 (t, J=7.2Hz, 2H), 7.91 (d, J=9.4Hz, 2H), 8.01 (d, J=7.4Hz, 2H).

Method 2: Place HSO3Cl (10mL) into a 50mL round-bottomed flask. 1-Phenylpyrrolidon-2-one (1 g, 6.21 mmol) was added to the mixture. The resulting solution was allowed to react overnight with stirring while maintaining the temperature at room temperature. The reaction mixture was then quenched by adding 100 mL H2O/ice. The resulting solution was extracted once with 100 mL CH2Cl2 and the organic layer was dried over MgSO4 and concentrated by evaporation under vacuum using a rotary evaporator. 0.7 g (43%) of 4-(2-oxo-1-pyrrolinyl)benzenesulfonyl chloride were obtained as a yellow solid. 1HNMR (400MHz, CDCl3, δ) 2.22 (2H, m), 2.71 (2H, t), 3.95 (2H, t), 7.88 (2H, t), 8.05 (2H, t). ES-MSm/z162[M+H]+.

Main reference materials

[1] Novel tertiary sulfonamides as potent anti-cancer agents