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Diisopropylamine → 1-Ethyl-3-(3,4,5-trimethoxyphenylthio)-1-(2-thienyl)propyl isocyanide

HRID 1722743
ノート
印刷プレビュー

反応式

HRID 1722743 の反応式
C(NC(C)C)(C)C.C([Li])CCC.CCCCCC.C([N-]C(C)C)(C)C.[Li+].[S:27]1[CH:31]=[CH:30][CH:29]=[C:28]1[CH:32]([N+:35]#[C-:36])[CH2:33][CH3:34].[CH3:37][O:38][C:39]1[CH:40]=[C:41]([S:49][CH2:50][CH2:51]Cl)[CH:42]=[C:43]([O:47][CH3:48])[C:44]=1[O:45][CH3:46]>O1CCCC1.CCOCC.C(O)(=O)C>[CH2:33]([C:32]([N+:35]#[C-:36])([C:28]1[S:27][CH:31]=[CH:30][CH:29]=1)[CH2:51][CH2:50][S:49][C:41]1[CH:40]=[C:39]([O:38][CH3:37])[C:44]([O:45][CH3:46])=[C:43]([O:47][CH3:48])[CH:42]=1)[CH3:34]
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

HCID 7912DiisopropylamineHCID 2724682Lithium diisopropylamideHCID 149941832-(3,4,5-Trimethoxyphenylthio)ethyl chlorideHCID 152885881-(2-Thienyl)propyl isocyanideHCID 178418244HCID 178418244、化合物

生成物 1

HCID 106910101-Ethyl-3-(3,4,5-trimethoxyphenylthio)-1-(2-thienyl)propyl isocyanide
収率 74.4%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

A solution of diisopropylamine (2.65 g) in tetrahydrofuran is cooled to -60° C. and 1.6M n-butyl lithium/hexane solution (14 ml) is added dropwise thereto in nitrogen atmosphere. The mixture is stirred at the same temperature, whereby the solution containing lithium diisopropylamide is obtained. A solution of 1-(2-thienyl)propyl isocyanide (2.8 g) in tetrahydrofuran is added dropwise to the solution obtained above at -60° C. and the mixture is stirred at the same temperature for 20 minutes. A solution of 2-(3,4,5-trimethoxyphenylthio)ethyl chloride (5.9 g) in tetrahydrofuran is added dropwise to the mixture at -60° C. and the mixture is stirred at -30° C. in nitrogen atmosphere for 2 hours. Acetic acid is added to the mixture to cease the reaction and ether is added to the reaction mixture. The mixture is washed, dried and concentrated under reduced pressure to remove solvent. The residue is purified by silica gel chromatography, whereby 1-ethyl-3-(3,4,5-trimethoxyphenylthio)-1-(2-thienyl)propyl isocyanide (5.2 g) is obtained as red oil.

後処理

  1. customis obtained
  2. customobtained above at -60° C.
  3. stirringthe mixture is stirred at the same temperature for 20 minutes
  4. stirringthe mixture is stirred at -30° C. in nitrogen atmosphere for 2 hours
  5. additionis added to the reaction mixture
  6. washThe mixture is washed
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customto remove solvent
  10. customThe residue is purified by silica gel chromatography

出典と根拠

ORDレコード
ord-4bc0e71f055b4fac883f1a2cebd824c3
出典データセット
uspto-grants-1989_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04857543

反応ノート

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