Sulfuryl chloride → N-(2-chloro-3,5-dimethoxyphenyl)acetamide
Reaction equation
S(Cl)([Cl:4])(=O)=O.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([NH:16][C:17](=[O:19])[CH3:18])[CH:11]=[C:12]([O:14][CH3:15])[CH:13]=1>C(C#N)(C)=O>[Cl:4][C:11]1[C:12]([O:14][CH3:15])=[CH:13][C:8]([O:7][CH3:6])=[CH:9][C:10]=1[NH:16][C:17](=[O:19])[CH3:18]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Sulfurylchloride (26.9 ml, 325 mmol, 1.93 eq.) is added (in 7 min) to a cold (0° C.) suspension of N-(3,5-dimethoxyphenyl)-acetamide (32.9 g, 169 mmol) in AcCN (500 ml), under an inert atmosphere. The resulting yellowish is allowed to stir 30 min and quenched by dropwise addition of a saturated aqueous solution of sodium bicarbonate (250 ml). The resulting precipitate is collected by vacuum filtration, washed with water (300 ml) and dried to afford 20 g of the desired product (batch 1). The filtrate is diluted with a saturated aqueous solution of sodium bicarbonate (300 ml) and extracted with EE (2×300 ml). The organic phase is washed with water and brine, dried (sodium sulphate), filtered and concentrated. The residue is purified by silica gel column chromatography (EE/Hx, 1:1→2:1) to provide 8.8 g of product (batch 2). Batch 1 and 2 are combined and stirred in hexane. The solid is collected by filtration, washed with hexane and dried to afford 25.8 g of the title compound as a white solid. ESI-MS: 264.0/266.0 [MH]+.