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

HRID 1349

Reaction equation

HRID 1349 reaction equation
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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3679fbd88dec487795772a47ae39b783
Source dataset
uspto-grants-1998_03
Patent number
US05723606

Linked notes

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