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Dimethylformamide → 2'-Cyanomethylspiro[benzofuran-2(3H),4'(2'H)-isoquinoline]

HRID 648103
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HRID 648103 반응식
CN(C)C=O.[CH2:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]2([CH2:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[O:16]2)[CH2:8][NH:7]1.C(=O)(O)[O-].[Na+].Cl[CH2:30][C:31]#[N:32]>O>[C:31]([CH2:30][N:7]1[CH2:8][C:9]2([CH2:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[O:16]2)[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:6]1)#[N:32]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 7856ChloroacetonitrileHCID 516892Sodium BicarbonateHCID 15917444spiro[benzofuran-2(3H),4'(2'H)-isoquinoline]

생성물 1

HCID 132645362'-Cyanomethylspiro[benzofuran-2(3H),4'(2'H)-isoquinoline]

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To dry dimethylformamide is added spiro[benzofuran-2(3H),4'(2'H)-isoquinoline] (11.0 g), sodium bicarbonate (8.4 g) and chloroacetonitrile (6.8 g) and the mixture is heated to 70° for four hours. The dimethylformamide is evaporated to give an oil, which is stirred with water (300 ml) for 15 minutes and then extracted with ether/dichloromethane. The organic extract is washed with water (2X), saturated sodium chloride solution and then dried over anhydrous magnesium sulfate. After filtering, the solvents are evaporated to an oil which solidifies to the product (10.6 g), 83%), as an off-white solid upon trituration with petroleum ether/ether. For analysis, a sample is recrystallized twice from hexane/acetone to yield platelets.

후처리

  1. temperaturethe mixture is heated to 70° for four hours
  2. customThe dimethylformamide is evaporated
  3. customto give an oil, which
  4. extractionextracted with ether/dichloromethane
  5. extractionThe organic extract
  6. washis washed with water (2X), saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationAfter filtering
  9. customthe solvents are evaporated to an oil which
  10. customFor analysis, a sample is recrystallized twice from hexane/acetone
  11. customto yield platelets

출처 및 근거

ORD 기록
ord-fc359672d031443485785603ea8bd0dd
출처 데이터셋
uspto-grants-1983_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04410699

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