反应 #1445

反应方程式

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

溶剂

water

dichloromethane

dichloromethane

triethylamine

反应条件

后处理

1. 1
   温度with cooling on an ice bath
2. 2
   浓缩the 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
   温度with cooling on an ice bath
5. 5
   workup.ADDITIONthe resulting solution was dropwise added to a solution
6. 6
   其他obtained
7. 7
   温度The reaction solution was warmed up to room temperature
8. 8
   其他The resulting reaction solution
9. 9
   其他subjected to phase separation
10. 10
    其他to separate dichloromethane layer which
11. 11
    洗涤was subsequently washed with 0.5N hydrochloric acid
12. 12
    干燥a saturated sodium bicarbonate aqueous solution and dried over anhydrous magnesium sulfate
13. 13
    其他After removing the solvent
14. 14
    workup.DISTILLATIONby distillation
15. 15
    其他the thus obtained residue was crystallized from toluene

实验过程

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.

来源