(2-Oxo-1,3-oxazolidin-4-yl)methyl 4-methylbenzene-1-sulfonate → (1,3-Oxazolidin-2-on-4-yl)methyl Thioacetate

HRID 622631Notes

Reaction equation

HRID 622631 reaction equation
C1(C)C=CC(S([O:10][CH2:11][CH:12]2[CH2:16][O:15][C:14](=[O:17])[NH:13]2)(=O)=O)=CC=1.[C:19]([O-])(=[S:21])[CH3:20].C([N+](CCCC)(CCCC)CCCC)CCC>CC(C)=O>[C:19]([O:10][CH2:11][CH:12]1[CH2:16][O:15][C:14](=[O:17])[NH:13]1)(=[S:21])[CH3:20]

Participants

4

Reactant 2

HCID 14456891(2-Oxo-1,3-oxazolidin-4-yl)methyl 4-methylbenzene-1-sulfonateHCID 178477078HCID 178477078, compound

Product 1

HCID 21291365(1,3-Oxazolidin-2-on-4-yl)methyl ThioacetateYield 75%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2-oxo-1,3-oxazolidin-4-ylmethyl p-toluenesulfonate (1.22 g., 0.0045 mole) and tetrabutylammonium thioacetate (1.71 g, 0.0054 mole) in 75 ml. acetone was refluxed under nitrogen for 90 min. The reaction mixture was concentrated to dryness and the residue was chromatographed on silica gel (250 g). Elution with 4:1 ethyl acetate-hexane yielded 580 mg. of the title compound (75% yield). NMR (CDCl3): 2.38 (s, 3H); 3.06 (d, 2H); 3.84-4.67 (c, 3H); and 6.3 (b, 1H)ppm.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customthe residue was chromatographed on silica gel (250 g)
  3. washElution with 4:1 ethyl acetate-hexane
  4. customyielded 580 mg

Sources & evidence

ORD record
ord-aed4ffe41a6e4aa181c5b3b60ce684b9
Source dataset
uspto-grants-1988_09
Patent number
US04772597

Reaction notes

Loading…