Potassium Carbonate → Ethyl (E)-3-(4-oxo-7-trifluoromethyl-4,5-dihydropyrrolo[1,2-a]-quinoxalin-1-yl)acrylate

HRID 576835

反応式

HRID 576835 の反応式
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-])=O.[CH2:15]([O:17][C:18](/[CH:20]=[CH:21]/[C:22]1[NH:26][C:25]([C:27](OCC)=[O:28])=[CH:24][CH:23]=1)=[O:19])[CH3:16].C(=O)([O-])[O-].[K+].[K+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(O)(=O)C.O.C(OCC)C.CS(C)=O>[O:28]=[C:27]1[NH:12][C:3]2[C:2](=[CH:7][CH:6]=[C:5]([C:8]([F:11])([F:10])[F:9])[CH:4]=2)[N:26]2[C:22](/[CH:21]=[CH:20]/[C:18]([O:17][CH2:15][CH3:16])=[O:19])=[CH:23][CH:24]=[C:25]12

参加物

9

反応物 4

HCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 677784-Fluoro-3-nitrobenzotrifluorideHCID 53836411H-Pyrrole-2-carboxylic acid, 5-[(1E)-3-ethoxy-3-oxo-1-propen-1-yl]-, ethyl ester

生成物 1

HCID 59198853Ethyl (E)-3-(4-oxo-7-trifluoromethyl-4,5-dihydropyrrolo[1,2-a]-quinoxalin-1-yl)acrylate収率 68.5%

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒2 回HCID 3283Diethyl Ether溶媒

反応条件

温度
100 °C

実験手順

A mixture of 1-fluoro-2-nitro-4-trifluoromethylbenzene 523 mg, ethyl 5-[(E)-2-ethoxycarbonylvinyl]-1H-pyrrole-2-carboxyate 593 mg, potassium carbonate 864 mg and dimethylsulfoxide 10 mL was heated at 100° C. for 3.5 hours. After cooling off the reaction liquid, 100 mL of diethyl ether was added, followed by filtration. To the filtrate 100 mL of water was added to separate the organic layer. The aqueous layer was extracted twice with 50 mL of diethyl ether, and the extract was combined with the organic layer, followed by washing three times with 20 mL of water and once with 20 mL of saturated brine by the order stated. After drying the same over magnesium sulfate, the solvent was distilled off under reduced pressure, leaving 965 mg of a brown, viscous substance. This was dissolved in a liquid mixture of 12 mL of acetic acid and 5 mL of water, and to the solution 1.31 g of sodium hyposulfite was added, followed by heating under reflux for 30 minutes. After cooling off the reaction liquid, 50 mL of water was added and the precipitated crystals were recovered by filtration. The crystals were washed with water and diethyl ether, and dried under heating to provide 600 mg of the title compound.

後処理

  1. temperatureAfter cooling off
  2. additionwas added
  3. filtrationfollowed by filtration
  4. additionTo the filtrate 100 mL of water was added
  5. customto separate the organic layer
  6. extractionThe aqueous layer was extracted twice with 50 mL of diethyl ether
  7. washby washing three times with 20 mL of water
  8. dry with materialAfter drying the same over magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customleaving 965 mg of a brown, viscous substance
  11. temperatureby heating
  12. temperatureunder reflux for 30 minutes
  13. temperatureAfter cooling off
  14. additionwas added
  15. filtrationthe precipitated crystals were recovered by filtration
  16. washThe crystals were washed with water and diethyl ether
  17. customdried
  18. temperatureunder heating

出典と根拠

ORDレコード
ord-e87a3c6e219d4881bf04a95840413dfd
出典データセット
uspto-grants-2015_05
特許番号
US09040536B2

関連ノート

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