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

HRID 648103
ノート
印刷プレビュー

反応式

HRID 648103 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fc359672d031443485785603ea8bd0dd
出典データセット
uspto-grants-1983_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04410699

反応ノート

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