Phosgene → HCID 9878953、化合物

HRID 558256ノート

反応式

HRID 558256 の反応式
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]

参加物

6

反応物 4

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

生成物 1

HCID 9878953HCID 9878953、化合物収率 125.2%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-98891153d7da47f69b65c81f27236953
出典データセット
uspto-grants-2011_11
特許番号
US08063044B2

反応ノート

読み込み中…