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

HRID 622629Notes

Reaction equation

[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[O:12]=[C:13]1[NH:17][CH:16]([CH2:18][OH:19])[CH2:15][O:14]1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:19][CH2:18][CH:16]2[CH2:15][O:14][C:13](=[O:12])[NH:17]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 25 °C

Procedure

p-Toluenesulfonyl chloride (1.01 g, 0.0053 mole) was added to a stirred solution of 2-oxo-1,3-oxazolidin-4-methanol (0.619 g, 0.0053 mole) and 4-dimethylaminopyridine (1.30 g, 0.0106 mole) in 60 ml. methylene chloride at 0° C. under an atmosphere of nitrogen. After 1 hour at 0° C., 0.121 g. more p-toluenesulfonyl chloride was added and the reaction mixture was stirred at 0° C. for 30 min. and at 25° C. for 1 hour. The reaction solution was then washed with two 50 ml. portions of 1N aqueous hydrochloric acid solution, 50 ml. water, 50 ml. saturated aqueous sodium bicarbonate solution and 50 ml. saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo to a white solid of the title compound (1.22 g, 85% yield). NMR (CDCl3): 2.45 (s, 3H); 3.87-4.54 (c, 5H); 6.18 (b, 1H); 7.3 (d, 2H); and 7.73 (d, 2H)ppm.

Workup

customat 0° C.
washThe reaction solution was then washed with two 50 ml
dry with materialsaturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate

Sources & evidence

ORD record: ord-b5c1b2d9258747a3b50e97f37c2ce10a
Source dataset: uspto-grants-1988_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04772597

Reaction notes

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