Thionyl Chloride → 3-(6,11-Dihydro-11-oxodibenz[b,e]oxepin-2-yl)propanyl chloride

HRID 1417088노트

반응식

HRID 1417088 반응식
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([CH2:17][CH2:18][C:19](O)=O)=[CH:16][C:3]1=2.S(Cl)([Cl:24])=O>CN(C)C=O.C(Cl)Cl>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([CH2:17][CH2:18][CH2:19][Cl:24])=[CH:16][C:3]1=2

참가 물질

5

반응물 2

HCID 24386Thionyl ChlorideHCID 123929606,11-Dihydro-11-oxodibenz[b,e]oxepin-2-propanoic acid

생성물 1

HCID 677979853-(6,11-Dihydro-11-oxodibenz[b,e]oxepin-2-yl)propanyl chloride

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

실험 절차

To a flask was added a few drops of N,N-dimethylformamide and 35.25 g of 3-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)propanoic acid in 500 ml of dry methylene chloride. The chilled stirring suspension was treated dropwise over several minutes with 11.0 ml of thionyl chloride. The suspension was warmed intermittently on a steam bath until all gas evolution ceased. The resulting solution was then allowed to reflux for 15 minutes and was allowed to stand at room temperature under nitrogen atmosphere overnight. The solution was concentrated in vacuo to an oil. The oil was dissolved in 500 ml of methylene chloride and was treated with another 11.0 ml of thionyl chloride. The solution was allowed to reflux for 3 hours and was again concentrated to an oil in vacuo. The oil still contained a significant amount of crystalline impurity, which was filtered away after triturating with a hexane/ether solution. The supernatant was concentrated to an oil in vacuo which solidified overnight in refrigeration. The purified solids were recrystallized from three portions of cyclohexane to give 25.03 g of 3-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)propanyl chloride, m.p. 69-72° C.

후처리

  1. temperatureThe suspension was warmed intermittently on a steam bath until all gas evolution
  2. temperatureto reflux for 15 minutes
  3. concentrationThe solution was concentrated in vacuo to an oil
  4. dissolutionThe oil was dissolved in 500 ml of methylene chloride
  5. additionwas treated with another 11.0 ml of thionyl chloride
  6. temperatureto reflux for 3 hours
  7. concentrationwas again concentrated to an oil in vacuo
  8. filtrationwas filtered away
  9. customafter triturating with a hexane/ether solution
  10. concentrationThe supernatant was concentrated to an oil in vacuo which
  11. waitsolidified overnight in refrigeration
  12. customThe purified solids were recrystallized from three portions of cyclohexane

출처 및 근거

ORD 기록
ord-93406e933e4947ea8d049ea1dfa232ed
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05917057

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