Phosgene → HCID 9878953, 화합물

HRID 558256노트

반응식

HRID 558256 반응식
ClC(Cl)=O.[Cl:5][C:6]1[CH:7]=[C:8](O)[CH:9]=[C:10]([Cl:12])[CH:11]=1.[C:14](=[O:17])([O-])[O-].[Cs+].[Cs+].O.[NH2:21][NH2:22]>CC(C)=O>[Cl:5][C:6]1[CH:7]=[C:8]([CH:9]=[C:10]([Cl:12])[CH:11]=1)[O:17][C:14]1[C:8]([CH2:9][CH3:10])=[N:21][NH:22][C:11]=1[CH2:6][CH3:7]

참가 물질

6

반응물 4

HCID 6371PhosgeneHCID 10796Cesium carbonateHCID 115713,5-DichlorophenolHCID 24654Hydrazine hydrate (1:1)

생성물 1

HCID 9878953HCID 9878953, 화합물수율 125.2%

시약·촉매·용매 1

HCID 180Acetone용매

반응 조건

온도
60 °C

실험 절차

A mixture of the chloroketone of Preparation 2 (5 g, 30.8 mmol), 3,5-dichlorophenol (5 g, 30.8 mmol), caesium carbonate (10 g, 30.8 mmol) and acetone (40 ml) was heated under reflux for 18 hours. After cooling, a solid was removed by filtration and washed with dichloromethane (100 ml). The combined filtrates were concentrated under reduced pressure. The crude product was dissolved in ethanol (20 ml), hydrazine hydrate (1.5 ml, 30.8 mmol) was added and the mixture was heated at 60° C. for 30 minutes under nitrogen. After cooling, the mixture was concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel eluting with ether:pentane (1:1, by volume) to provide the title compound (5.5 g) as a yellow oil which solidified on standing to leave a yellow solid, m.p. 114-115° C.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. temperatureAfter cooling
  4. customa solid was removed by filtration
  5. washwashed with dichloromethane (100 ml)
  6. concentrationThe combined filtrates were concentrated under reduced pressure
  7. dissolutionThe crude product was dissolved in ethanol (20 ml)
  8. temperatureAfter cooling
  9. concentrationthe mixture was concentrated under reduced pressure
  10. customthe residue was purified by flash chromatography on silica gel eluting with ether:pentane (1:1, by volume)

출처 및 근거

ORD 기록
ord-98891153d7da47f69b65c81f27236953
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063044B2

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