Hydrochloric Acid → 2-Phenyl-3-[3-(diethylamino)propionyl]benzofuran

HRID 436495

반응식

HRID 436495 반응식
[C:1]1([C:7]2[O:8][C:9]3[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=3[C:11]=2[C:12](=[O:14])[CH3:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:19]=O.Cl.[CH2:22]([NH:24][CH2:25][CH3:26])[CH3:23].Cl>C(O)(C)C.C(O)C>[C:1]1([C:7]2[O:8][C:9]3[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=3[C:11]=2[C:12](=[O:14])[CH2:13][CH2:19][N:24]([CH2:25][CH3:26])[CH2:22][CH3:23])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 10197650Diethylammonium chlorideHCID 130247261-(2-Phenylbenzofuran-3-yl)ethanone

생성물 1

HCID 214527612-Phenyl-3-[3-(diethylamino)propionyl]benzofuran

시약·촉매·용매 2

HCID 702Ethanol용매HCID 3776Isopropanol용매

실험 절차

To a solution of 47.2 grams of 2-phenyl-3-acetyl benzofuran in 150 milliliters of isopropanol, were added 8.4 grams of paraformaldehyde, 30.8 grams of diethylamine hydrochloride and 3 milliliters of a saturated solution of hydrogen chloride in ethanol and the mixture was heated at its boiling point under reflux for 8 hours. The solvent was then evaporated from the mixture under vacuum and the residue was triturated with water and the insoluble portion thereof was extracted therefrom with ethyl ether. The aqueous solution was made alkaline by the addition of a 5% aqueous sodium hydroxide solution and the oily base which separated was extracted with ethyl ether. After drying the ether extract over anhydrous sodium sulfate a solution of hydrogen chloride in ethanol was added thereto and the crystalline hydrochloride of the compound named in the heading of this example precipitated. The crystals thus obtained were recrystallized in a mixture of ethanol and ethyl ether. In this manner, 34.2 grams of the recrystallized hydrochloride, which had a melting point of 113°-115°C, was obtained.

후처리

  1. temperaturethe mixture was heated at its boiling point
  2. temperatureunder reflux for 8 hours
  3. customThe solvent was then evaporated from the mixture under vacuum
  4. customthe residue was triturated with water
  5. extractionthe insoluble portion thereof was extracted
  6. additionby the addition of a 5% aqueous sodium hydroxide solution
  7. customthe oily base which separated
  8. extractionwas extracted with ethyl ether
  9. dry with materialAfter drying the ether
  10. extractionextract over anhydrous sodium sulfate a solution of hydrogen chloride in ethanol
  11. additionwas added
  12. customprecipitated
  13. customThe crystals thus obtained
  14. customwere recrystallized in a mixture of ethanol and ethyl ether
  15. customwas obtained

출처 및 근거

ORD 기록
ord-ae2794e25b984ca29a251a1e2a2d4fdd
출처 데이터셋
uspto-grants-1977_02
특허 번호
US04009184

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