Potassium Carbonate → ethyl 6-(trifluoromethyl)-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate

HRID 1448472ノート

反応式

HRID 1448472 の反応式
C(=O)([O-])[O-].[K+].[K+].[NH2:7][C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:9]=1[OH:18].Br[CH:20]([CH2:26]Br)[C:21]([O:23][CH2:24][CH3:25])=[O:22]>CC(C)=O>[F:17][C:14]([F:15])([F:16])[C:12]1[CH:11]=[CH:10][C:9]2[O:18][CH:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:26][NH:7][C:8]=2[CH:13]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 97945Ethyl 2,3-dibromopropionateHCID 1202462-Amino-4-(trifluoromethyl)phenol

生成物 1

HCID 11747775ethyl 6-(trifluoromethyl)-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

11.4 g of potassium carbonate was added to 48.7 g of 7B in 320 ml of acetone. Then 18.2 of ethyl 2,3-dibromopropionate was added dropwise to the refluxing mixture. This procedure was repeated thrice. The mixture was refluxed for 17 hours and filtered, and the filtrate was stripped of solvent under reduced pressure. The residue was dissolved in ether; the solution was washed with dilute sodium hydroxide solution, then dried (MgSO4) and stripped of solvent. The residue was washed with petroleum ether and dried. The residue was mixed with ether and filtered. Part of the solvent was evaporated from the filtrate; the remaining solution was cooled. Crystals which formed were filtered and recrystallized from ether to give 7, m.p.: 105°-107°.

後処理

  1. temperatureThe mixture was refluxed for 17 hours
  2. filtrationfiltered
  3. dissolutionThe residue was dissolved in ether
  4. washthe solution was washed with dilute sodium hydroxide solution
  5. dry with materialdried (MgSO4)
  6. washThe residue was washed with petroleum ether
  7. customdried
  8. additionThe residue was mixed with ether
  9. filtrationfiltered
  10. customPart of the solvent was evaporated from the filtrate
  11. temperaturethe remaining solution was cooled
  12. customCrystals which formed
  13. filtrationwere filtered
  14. customrecrystallized from ether
  15. customto give 7, m.p.: 105°-107°

出典と根拠

ORDレコード
ord-a749377ba5bf43f5b37a59353094a98a
出典データセット
uspto-grants-1979_12
特許番号
US04180572

反応ノート

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