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

HRID 2164757ノート

反応式

HRID 2164757 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1df774c1be6a4a7c88cfcb09b684cb58
出典データセット
uspto-grants-1985_03
特許番号
US04507308

反応ノート

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