Imidazole → 4-(3,4-Dichlorophenyl)-5-(imidazol-1-yl)pent-1-ene

HRID 1533044노트

반응식

HRID 1533044 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:13]OS(C)(=O)=O)[CH2:10][CH:11]=[CH2:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[NH:19]1[CH:23]=[CH:22][N:21]=[CH:20]1.ClCCl.CO>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:13][N:19]2[CH:23]=[CH:22][N:21]=[CH:20]2)[CH2:10][CH:11]=[CH2:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 887MethanolHCID 6344DichloromethaneHCID 226137984-(3,4-Dichlorophenyl)-5-(methanesulphonyloxy)pent-1-ene

생성물 1

HCID 226138214-(3,4-Dichlorophenyl)-5-(imidazol-1-yl)pent-1-ene수율 70.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

4-(3,4-Dichlorophenyl)-5-(methanesulphonyloxy)pent-1-ene (5.4 g) (see Preparation 23) and imidazole (3.6 g) were dissolved in anhydrous acetonitrile (40 ml) and the mixture heated under reflux for 100 hours. The solvent was removed under reduced pressure, the residue dissolved in dichloromethane and the solvent removed under reduced pressure. The residue was dissolved in dichloromethane (100 ml) and washed with sufficient aqueous sodium carbonate solution to ensure that the aqueous phase reached pH14. The two phases were separated and the aqueous phase extracted with dichloromethane (100 ml). The organic phases were combined and the solvent removed under reduced pressure to give a residue which was chrornatographed on silica gel eluting with a solvent gradient of 100:0 changing to 98:2, by volume, dichloromethane:methanol, to give 4-(3,4-dichlorophenyl)-5-(imidazol-1-yl)pent-1-ene (3.45 g) as an orange oil.

후처리

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 100 hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue dissolved in dichloromethane
  5. customthe solvent removed under reduced pressure
  6. dissolutionThe residue was dissolved in dichloromethane (100 ml)
  7. washwashed with sufficient aqueous sodium carbonate solution
  8. customThe two phases were separated
  9. extractionthe aqueous phase extracted with dichloromethane (100 ml)
  10. customthe solvent removed under reduced pressure
  11. customto give a residue which

출처 및 근거

ORD 기록
ord-54a78e6ecbe24bd29614ce852721b275
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06207678B1

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