반응 #1445

반응 방정식

oxalyl chloride

dimethylformamide

2-methoxybiphen-4-ylcarboxylic acid

5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine

→

1-(2'-methoxybiphen-4-ylcarbonyl)-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine

용매

water

dichloromethane

dichloromethane

triethylamine

반응 조건

후처리

1. 1
   온도with cooling on an ice bath
2. 2
   농축the reaction solution was concentrated under a reduced pressure
3. 3
   workup.DISSOLUTIONThe thus obtained residue was dissolved in 8.4 ml of dichloromethane
4. 4
   온도with cooling on an ice bath
5. 5
   workup.ADDITIONthe resulting solution was dropwise added to a solution
6. 6
   기타obtained
7. 7
   온도The reaction solution was warmed up to room temperature
8. 8
   기타The resulting reaction solution
9. 9
   기타subjected to phase separation
10. 10
    기타to separate dichloromethane layer which
11. 11
    세척was subsequently washed with 0.5N hydrochloric acid
12. 12
    건조a saturated sodium bicarbonate aqueous solution and dried over anhydrous magnesium sulfate
13. 13
    기타After removing the solvent
14. 14
    workup.DISTILLATIONby distillation
15. 15
    기타the thus obtained residue was crystallized from toluene

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.

출처