Water → 3-[[3-Chloro-2-[(phenylmethyl)thio]phenyl]methyl]-2-oxazolidinone

HRID 703041Notes

Reaction equation

[H-].[Na+].[O:3]1[CH2:7][C:6](=O)[N:5]=[C-:4]1.[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16]Cl)[C:11]=1[S:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[OH2:26]>CN(C)C=O.CCCCCC.C(OCC)(=O)C>[Cl:9][C:10]1[C:11]([S:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:12]([CH2:16][N:5]2[CH2:6][CH2:7][O:3][C:4]2=[O:26])[CH:13]=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a Suspension of 0.9 g sodium hydride (hexane washed) in 15 mL of N,N-dimethylformamide, a solution of 3.05 g of 2-oxazolidone in 15 mL of N,N-dimethylformamide was added at room temperature. As a white precipitate formed, the mixture was heated slowly to 80° C. over 30 minutes and kept at 80° C. for another 30 minutes. The mixture was cooled to room temperature, and a solution of 8.5 g of the compound of Example 3 in 20 mL of N,N-dimethylformamide was added in one portion. The resulting solution was stirred at 25° C. for 12 hours, poured into 50 mL water and extracted with ethyl acetate. The organic layer was washed well with water, dried over magnesium sulfate, filtered, and the filtrate evaporated to leave a yellow oil. Silica gel flash chromatography (4:1 hexane-ethyl acetate eluant) afforded after evaporation of the eluant 7.5 g of the subject compound as a yellow oil.

Workup

customAs a white precipitate formed
temperatureThe mixture was cooled to room temperature
extractionextracted with ethyl acetate
washThe organic layer was washed well with water
dry with materialdried over magnesium sulfate
filtrationfiltered
customthe filtrate evaporated
customto leave a yellow oil
customafter evaporation of the eluant 7.5 g of the subject compound as a yellow oil

Sources & evidence

ORD record: ord-b39436c60024496884aaa39d661dfa73
Source dataset: uspto-grants-1991_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04981506

Reaction notes

Loading…