Isopropanol → 2-(3-Chloropropyl)-1H-isoindole-1,3(2H)-dione

HRID 5273

반응식

HRID 5273 반응식
C(O)(C)C.[ClH:5].CNOC.Br[CH2:11][CH2:12][CH2:13][N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24].C(=O)(O)[O-].[Na+]>C(N(CC)CC)C>[Cl:5][CH2:11][CH2:12][CH2:13][N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24]

참가 물질

6

반응물 4

HCID 3776IsopropanolHCID 21611N-3-BromopropylphthalimideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 516892Sodium Bicarbonate

생성물 1

HCID 2452652-(3-Chloropropyl)-1H-isoindole-1,3(2H)-dione수율 46.1%

시약·촉매·용매 1

HCID 8471Triethylamine용매

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.

후처리

  1. temperaturethe mixture was refluxed for 33 hours
  2. extractionextracted with chloroform
  3. customThe organic layer was separated
  4. washwas washed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationChloroform was distilled off
  7. customthe residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-a7a6cc20410049fab1aec4b794941182
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05244487

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