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

HRID 548631Notes

Reaction equation

CN1C=CN=C1.[OH:7][CH2:8][CH:9]1[CH2:13][O:12][C:11](=[O:14])[NH:10]1.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>ClCCl>[CH3:25][C:15]1[CH:20]=[CH:19][C:18]([S:21]([O:7][CH2:8][CH:9]2[CH2:13][O:12][C:11](=[O:14])[NH:10]2)(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

waitat room temperature for 24 hours
customThe mixture is then quenched
stirringunder vigorous stirring with 0.5 ml of water
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
dry with materialis dried over magnesium sulfate
concentrationThe organic layer is concentrated in vacuo

Sources & evidence

ORD record: ord-f4ba0346a6fd48c0baec5272191de0e9
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07943605B2

Reaction notes

Loading…