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

HRID 2164757노트

반응식

HRID 2164757 반응식
[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

참가 물질

4

반응물 2

HCID 756333-(2-Chloroethyl)-1,3-oxazolidin-2-oneHCID 23670929N-(8-trifluoromethyl-4-quinolyl)-anthranilic acid sodium salt

생성물 1

HCID 13136717N-(8-trifluoromethyl-4-quinolyl)-anthranilic acid beta-(2-oxo-3-oxazolidinyl)-ethyl ester수율 44.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

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.

후처리

  1. temperaturewas heated
  2. customUpon completion of the reaction
  3. temperaturethe mixture was cooled
  4. filtrationfiltered
  5. additionpoured into 300 ml of water
  6. extractionThe crude product was extracted with ethyl acetate
  7. customthe solvent evaporated off
  8. customthe residue crystallized from ethanol

출처 및 근거

ORD 기록
ord-1df774c1be6a4a7c88cfcb09b684cb58
출처 데이터셋
uspto-grants-1985_03
특허 번호
US04507308

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