3-(2-Chloroethyl)-1,3-oxazolidin-2-one → HCID 13136716, compound

HRID 2164756Notes

Reaction equation

[Na+].[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][C:14]3[C:15](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:16]([O-:18])=[O:17])=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.Cl[CH2:24][CH2:25][N:26]1[CH2:30][CH2:29][O:28][C:27]1=[O:31]>CN(C)C=O>[O:31]=[C:27]1[N:26]([CH2:25][CH2:24][O:17][C:16](=[O:18])[C:15]2[C:14](=[CH:22][CH:21]=[CH:20][CH:19]=2)[NH:13][C:7]2[C:6]3[C:11](=[CH:12][C:3]([Cl:2])=[CH:4][CH:5]=3)[N:10]=[CH:9][CH:8]=2)[CH2:30][CH2:29][O:28]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture comprising 12.8 g of N-(7-chloro-4-quinolyl)-anthranilic acid sodium salt, 6.64 g of 90% 3-(β-chloroethyl)-oxazolidine-2-one and 80 ml of dimethylformamide was heated under stirring at 120° C. for five hours. Upon completion of the reaction, the mixture was cooled, filtered, and the solvent eliminated in vacuo. To the residue, 80 ml of ether were added and the solid thus obtained was collected on filter and purified by chromatography on a silica gel column using ethyl acetate as eluent. The desired product was crystallized from isopropanol to give 11.2 g of N-(7-chloro-4-quinolyl)-anthranilic acid β-(2-oxo-3-oxazolidinyl)-ethyl ester, melting at 122°-124° C.

Workup

temperaturewas heated
customUpon completion of the reaction
temperaturethe mixture was cooled
filtrationfiltered
additionTo the residue, 80 ml of ether were added
customthe solid thus obtained
customwas collected
filtrationon filter
custompurified by chromatography on a silica gel column
customThe desired product was crystallized from isopropanol

Sources & evidence

ORD record: ord-c8f714e3fda8479698eb1d37a52888f0
Source dataset: uspto-grants-1985_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04507308

Reaction notes

Loading…