تفاعل #1445

معادلة التفاعل

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

المذيبات

water

dichloromethane

dichloromethane

triethylamine

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwith cooling on an ice bath
2. 2
   تركيزthe 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
   درجة الحرارةwith cooling on an ice bath
5. 5
   workup.ADDITIONthe resulting solution was dropwise added to a solution
6. 6
   أخرىobtained
7. 7
   درجة الحرارةThe reaction solution was warmed up to room temperature
8. 8
   أخرىThe resulting reaction solution
9. 9
   أخرىsubjected to phase separation
10. 10
    أخرىto separate dichloromethane layer which
11. 11
    غسيلwas subsequently washed with 0.5N hydrochloric acid
12. 12
    تجفيفa saturated sodium bicarbonate aqueous solution and dried over anhydrous magnesium sulfate
13. 13
    أخرىAfter removing the solvent
14. 14
    workup.DISTILLATIONby distillation
15. 15
    أخرىthe thus obtained residue was crystallized from toluene

الإجراء التجريبي

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.

المصدر