3-(2-Chloroethyl)-1,3-oxazolidin-2-one → HCID 13136719, compound

HRID 2164758Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture comprising 10.62 g of N-(7-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, insoluble sodium chloride was filtered off, and the solvent was evaporated off in vacuo. The residue was treated with 200 ml of water and the solid, collected by filtration, crystallized from methylene dichloride: petroleum ether. 8.7 g of N-(7-trifluoromethyl-4-quinolyl)-anthranilic acid β-(2-oxo-3-oxazolidinyl)-ethyl ester, melting at 124°-125° C., were obtained.

Workup

temperaturewas heated
customUpon completion of the reaction
temperaturethe mixture was cooled
filtrationinsoluble sodium chloride was filtered off
customthe solvent was evaporated off in vacuo
additionThe residue was treated with 200 ml of water
filtrationthe solid, collected by filtration
customcrystallized from methylene dichloride

Sources & evidence

ORD record: ord-caf489528e1d4257a34300b2f79660e0
Source dataset: uspto-grants-1985_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04507308

Reaction notes

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