1-Methylimidazole → (2-Oxo-1,3-oxazolidin-4-yl)methyl 4-methylbenzene-1-sulfonate

N-methylimidazole (360 ml, 4.5 mmol, 1.5 eq) is added to a cooled suspension of 4-(hydroxymethyl)-1,3-oxazolidin-2-one a90 (0.35 g, 3 mmol, 1 eq) in dichloromethane (20 ml). p-Toluenesulfonyl chloride a40 (0.63 g, 3.3 mmol, 1.1 eq) in dichloromethane (5 ml) is then added, dropwise. The mixture is stirred at 0° C. for 5 hours then at room temperature for 24 hours. The mixture is then quenched under vigorous stirring with 0.5 ml of water and taken up in chloroform (100 ml). The organic phase is washed with a saturated aqueous solution of sodium hydrogenocarbonate (2×25 ml), with a 1N solution of hydrochloric acid (2×25 ml), with brine, and is dried over magnesium sulfate. The organic layer is concentrated in vacuo to afford 0.61 g of (2-oxo-1,3-oxazolidin-4-yl)methyl 4-methylbenzenesulfonate a91 as a white solid.

1. waitat room temperature for 24 hours
2. customThe mixture is then quenched
3. stirringunder vigorous stirring with 0.5 ml of water
4. washThe organic phase is washed with a saturated aqueous solution of sodium hydrogenocarbonate (2×25 ml), with a 1N solution of hydrochloric acid (2×25 ml), with brine
5. dry with materialis dried over magnesium sulfate
6. concentrationThe organic layer is concentrated in vacuo

ORD record

ord-f4ba0346a6fd48c0baec5272191de0e9

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07943605B2