Preparation method of 4-butylbenzene-1-sulfonyl chloride_Kain Industrial Additive

Background and overview^[1]

4-Butylbenzene-1-sulfonyl chloride can be used as a pharmaceutical synthesis intermediate. If 4-butylphenyl-1-sulfonyl chloride is inhaled, move the patient to fresh air; if skin contact occurs, take off contaminated clothing, rinse the skin thoroughly with soap and water, and seek medical attention if you feel unwell; if the eye contact If exposed to sunlight, separate eyelids, rinse with running water or saline, and seek medical attention immediately; if ingested, rinse mouth immediately, do not induce vomiting, and seek medical attention immediately.

Preparation^[1]

4-Butylbenzene-1-sulfonyl chloride was prepared as follows: To a solution of butylbenzene (4.13g, 30.8mmol) in CHCl3 (50mL) was added chlorosulfonic acid (17mL, 29.8g, 256mmol) and the mixture was brought to room temperature. Stir for 20 hours. The mixture was poured onto ice (200 mL) and extracted with EtOAc (3 x 100 mL). The combined extracts were washed with water, NaHCO3 solution and water, dried (Na2SO4), and concentrated in vacuo. The yellow oily residue 4-butylbenzene-1-sulfonyl chloride (yield 88%) can be used in the next reaction without further purification; 1HNMR (300MHz, CDCl3) δ0.94 (t, 3H, J=7Hz), 1.34- 1.41 (m, 2H), 1.62-1.67 (m, 2H), 2.73 (t, 2H, J=8Hz), 7.41 (d, 2H, J=8Hz), 7.94 (d, 2H, J=8Hz).

Apply^[1]

4-Butylbenzene-1-sulfonyl chloride can be used as a pharmaceutical synthesis intermediate, such as preparing 4-butyl-N-q.3.4-thiadiazole-2-benzosulfonamide: under argon, at -20 To a stirred solution of 2-amino-1,3,4-thiadiazole (2.0 g, 19.7 mmol) in pyridine (30 mL) at ℃, 4-butylphenyl-1-sulfonyl chloride (10 mmol) was added. The reaction mixture was stirred at room temperature for 16 hours. Water (300 mL) was added to quench the reaction. The mixture was extracted with CH2Cl2, and the organic extracts were washed with 2NHCl (2 × 150 mL), brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel, eluting with methanol:DCM 1:33, to give the product 4-butyl-N-q.3.4-thiadiazole-2-benzosulfonamide (3.72 g, 11.4 mmol, 58% yield ), solid, mp125-126℃.