3-Chloropropanesulphonyl chloride → HCID 71251904, compound

HRID 2411159Notes

Reaction equation

HRID 2411159 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([N:12]2[CH2:16][CH2:15][O:14][C:13]2=[O:17])[CH:3]=1.Cl[CH2:19][CH2:20][CH2:21][S:22](Cl)(=[O:24])=[O:23]>>[O:23]=[S:22]1(=[O:24])[CH2:21][CH2:20][CH2:19][N:1]1[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([N:12]2[CH2:16][CH2:15][O:14][C:13]2=[O:17])[CH:3]=1

Participants

3

Reactant 2

HCID 154103-Chloropropanesulphonyl chlorideHCID 86676754HCID 86676754, compound

Product 1

HCID 71251904HCID 71251904, compound

Procedure

To a mixture of methyl 2-bromo-4-nitrobenzoate (2 g), oxazolidin-2-one (0.67 g), potassium carbonate (2.06 g), copper(I) iodide (0.73 g) and N,N′-dimethylethylenediamine (0.83 mL) was added toluene (16 mL), and the mixture was stirred with heating under reflux for 8 hr. The reaction mixture was cooled, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give methyl 4-nitro-2-(2-oxo-oxazolidin-3-yl)benzoate (960 mg). To a solution of ethanol (24 mL) and water (5 mL) were added ammonium chloride (0.11 g) and iron (0.79 g), and a solution of the obtained methyl 4-nitro-2-(2-oxooxazolidin-3-yl)benzoate (960 mg) in ethanol (19 mL) was added while stirring at 60° C.-70° C. After completion of the reaction, the insoluble material was collected by filtration, and the filtrate was concentrated. To the obtained residue was added aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The solvent was evaporated from the organic layer to give methyl 4-amino-2-(2-oxooxazolidin-3-yl)benzoate (730 mg). Using the obtained methyl 4-amino-2-(2-oxooxazolidin-3-yl)benzoate (730 mg) and 3-chloropropane-1-sulfonyl chloride (0.49 mL) and by the reaction and treatment in the same manner as in Preparation Example 17, the title compound (495 mg) was obtained.

Workup

  1. customby the reaction and treatment in the same manner
  2. customas in Preparation Example 17

Sources & evidence

ORD record
ord-41b70533f3db478ea33a70427c5bff38
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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