4-Toluenesulfonyl chloride → 2-(2-Oxooxazolidin-3-yl)ethyl 4-methylbenzenesulfonate

HRID 1883027Notes

Reaction equation

HRID 1883027 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][O:6][C:5]1=[O:9].C(N(CC)CC)C.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>ClCCl.CN(C1C=CN=CC=1)C>[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23]([O:1][CH2:2][CH2:3][N:4]2[CH2:8][CH2:7][O:6][C:5]2=[O:9])(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 768872-Oxazolidinone, 3-(2-hydroxyethyl)-

Product 1

HCID 157609472-(2-Oxooxazolidin-3-yl)ethyl 4-methylbenzenesulfonateYield 73%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To an ice cold stirring solution of crude 3-(2-hydroxy-ethyl)oxazolidin-2-one (15.1 g, 115 mmol) in dichloromethane (40 mL) was added triethylamine (18 mL, 129 mmol), and 4-(N,N-dimethylamino)pyridine (0.143 g, 1.2 mmol). A slurry of 4-toluenesulfonyl chloride (25.0 g, 131 mmol) in dichloromethane (50 mL) was then added dropwise. The reaction mixture was stirred for 3 d at room temperature, washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was slurried in isopropanol and filtered to give 23.88 g (73%) of a white solid.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. filtrationfiltered

Sources & evidence

ORD record
ord-165ad4ad5949438b8dae0c0f324240b7
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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