Sulfuryl chloride → N-(2-chloro-3,5-dimethoxyphenyl)acetamide

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Reaction Steps

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]+.

Provenance & Evidence