반응 #5369

반응 방정식

isopropanol

N,O-dimethylhydroxylamine hydrochloride

sodium bicarbonate

N-(3-bromopropyl)phthalimide

→

N-(3-chloropropyl)phthalimide

수율 46.1%

용매

triethylamine

반응 조건

후처리

1. 1
   온도the mixture was refluxed for 33 hours
2. 2
   추출extracted with chloroform
3. 3
   기타The organic layer was separated
4. 4
   세척was washed with water
5. 5
   건조dried over magnesium sulfate
6. 6
   workup.DISTILLATIONChloroform was distilled off
7. 7
   기타the residue was purified by column chromatography on silica gel

실험 절차

To a suspension of 50 mol of isopropanol containing N,O-dimethylhydroxylamine hydrochloride (3.97 g, 40.0 mmol) was added dropwise 5.56 ml of triethylamine. After 5 minutes, there was added 2.68 g (10.0 mmol) of N-(3-bromopropyl)phthalimide and the mixture was refluxed for 33 hours. This was cooled to room temperature, then poured into 200 ml of saturated aqueous solution of sodium bicarbonate and extracted with chloroform. The organic layer was separated and was washed with water and dried over magnesium sulfate. Chloroform was distilled off and the residue was purified by column chromatography on silica gel. Development with 30% hexane-chloroform resulted in elution of 1.03 g of N-(3-chloropropyl)phthalimide and further development with chloroform resulted in 1.21 g (yield: 53%) of white crystals of N-[3-(N-methoxy-N-methylamino)propyl]-phthalimide.

출처