Pyridine → N-(4-ethynylphenyl)methanesulfonamide

Reaction equation

[C:1]([C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1)#[CH:2].N1C=CC=CC=1.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C([O-])(O)=O.[Na+]>[C:1]([C:3]1[CH:9]=[CH:8][C:6]([NH:7][S:17]([CH3:16])(=[O:19])=[O:18])=[CH:5][CH:4]=1)#[CH:2]

Participants

Procedure

step 1—To a solution of 4-ethynyl aniline (4.00 g, 34.00 mmol) DCM (60 mL) at 0° C. was added sequentially pyridine (3.32 mL, 40.8 mmol) and dropwise addition of methanesulfonyl chloride (3.17 mL, 40.80 mmol). The reaction was stirred and allowed to warm from 0° C. to RT over 3 h then poured into a saturated aqueous NaHCO3 (150 mL). The aqueous layer was separated and extracted with DCM (2×100 mL). The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified by SiO2 chromatography eluting with 20% EtOAc/hexanes to afford 5.92 g (88%) of N-(4-ethynyl-phenyl)-methanesulfonamide (80) as a solid.