Dimethylformamide → 1-(2'-Methoxybiphen-4-ylcarbonyl)-5-oxo-2,3,4,5-tetrahydro-1h-1-benzazepine

HRID 1349

반응식

HRID 1349 반응식
CO[C:3]1[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][CH:6]=[C:7]([C:9]([OH:11])=O)[CH:8]=1.C(Cl)(=O)[C:19](Cl)=[O:20].CN(C)C=O.[O:29]=[C:30]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[NH:34][CH2:33][CH2:32][CH2:31]1>ClCCl.O.C(N(CC)CC)C>[CH3:19][O:20][C:17]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:4]1[CH:3]=[CH:8][C:7]([C:9]([N:34]2[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[C:30](=[O:29])[CH2:31][CH2:32][CH2:33]2)=[O:11])=[CH:6][CH:5]=1

참가 물질

8

반응물 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 2947881,2,3,4-Tetrahydro-benzo(b)azepin-5-oneHCID 179973922-Methoxy-[1,1'-biphenyl]-4-carboxylic acid

생성물 1

HCID 543358131-(2'-Methoxybiphen-4-ylcarbonyl)-5-oxo-2,3,4,5-tetrahydro-1h-1-benzazepine

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매2회HCID 8471Triethylamine용매

실험 절차

A 1.67 g portion of 2-methoxybiphen-4-ylcarboxylic acid was dissolved in 17 ml of dichloromethane, 0.95 ml of oxalyl chloride and a catalytically effective amount of dimethylformamide were added to the resulting solution with cooling on an ice bath and then the resulting mixture was warmed up to room temperature. When completion of foaming was confirmed, the reaction solution was concentrated under a reduced pressure and subjected to azeotropic treatment with toluene twice. The thus obtained residue was dissolved in 8.4 ml of dichloromethane and, with cooling on an ice bath, the resulting solution was dropwise added to a solution obtained by dissolving 1.0 g of 5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine and 1.53 ml of triethylamine in 10 ml of dichloromethane. The reaction solution was warmed up to room temperature and the stirring was continued for 1 hour. The resulting reaction solution was mixed with water and subjected to phase separation to separate dichloromethane layer which was subsequently washed with 0.5N hydrochloric acid and a saturated sodium bicarbonate aqueous solution and dried over anhydrous magnesium sulfate. After removing the solvent by distillation, the thus obtained residue was crystallized from toluene to obtain 1.65 g of 1-(2'-methoxybiphen-4-ylcarbonyl)-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine as crude crystals.

후처리

  1. temperaturewith cooling on an ice bath
  2. concentrationthe reaction solution was concentrated under a reduced pressure
  3. dissolutionThe thus obtained residue was dissolved in 8.4 ml of dichloromethane
  4. temperaturewith cooling on an ice bath
  5. additionthe resulting solution was dropwise added to a solution
  6. customobtained
  7. temperatureThe reaction solution was warmed up to room temperature
  8. customThe resulting reaction solution
  9. customsubjected to phase separation
  10. customto separate dichloromethane layer which
  11. washwas subsequently washed with 0.5N hydrochloric acid
  12. dry with materiala saturated sodium bicarbonate aqueous solution and dried over anhydrous magnesium sulfate
  13. customAfter removing the solvent
  14. distillationby distillation
  15. customthe thus obtained residue was crystallized from toluene

출처 및 근거

ORD 기록
ord-3679fbd88dec487795772a47ae39b783
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05723606

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