3-(2-Chloroethyl)-1,3-oxazolidin-2-one → N-(8-trifluoromethyl-4-quinolyl)-anthranilic acid beta-(2-oxo-3-oxazolidinyl)-ethyl ester

HRID 2164757Notes

Reaction equation

[Na+].[F:2][C:3]([F:25])([F:24])[C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[C:9]2[NH:14][C:15]1[C:16](=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:17]([O-:19])=[O:18].Cl[CH2:27][CH2:28][N:29]1[CH2:33][CH2:32][O:31][C:30]1=[O:34]>CN(C)C=O>[O:34]=[C:30]1[N:29]([CH2:28][CH2:27][O:18][C:17](=[O:19])[C:16]2[C:15](=[CH:23][CH:22]=[CH:21][CH:20]=2)[NH:14][C:9]2[C:8]3[C:13](=[C:4]([C:3]([F:24])([F:2])[F:25])[CH:5]=[CH:6][CH:7]=3)[N:12]=[CH:11][CH:10]=2)[CH2:33][CH2:32][O:31]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture comprising 10.62 g of N-(8-trifluoromethyl-4-quinolyl)-anthranilic acid sodium salt, 4.98 g of 90% 3-(β-chloroethyl)-oxazolidin-2-one and 60 ml of dimethylformamide was heated under stirring at 120° C. for five hours. Upon completion of the reaction, the mixture was cooled, filtered, and poured into 300 ml of water. The crude product was extracted with ethyl acetate, the solvent evaporated off and the residue crystallized from ethanol to give 6 g of N-(8-trifluoromethyl-4-quinolyl)-anthranilic acid β-(2-oxo-3-oxazolidinyl)-ethyl ester, melting at 158°-160° C.

Workup

temperaturewas heated
customUpon completion of the reaction
temperaturethe mixture was cooled
filtrationfiltered
additionpoured into 300 ml of water
extractionThe crude product was extracted with ethyl acetate
customthe solvent evaporated off
customthe residue crystallized from ethanol

Sources & evidence

ORD record: ord-1df774c1be6a4a7c88cfcb09b684cb58
Source dataset: uspto-grants-1985_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04507308

Reaction notes

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