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Hexamethylphosphoramide → 2-(Benzhydrylideneamino)-3-quinolin-4-yl-butyronitrile

HRID 1597365
ノート
印刷プレビュー

反応式

HRID 1597365 の反応式
[CH:1]1[CH:6]=[CH:5][C:4]([C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:8][CH2:9][C:10]#[N:11])=[CH:3][CH:2]=1.CN(P(N(C)C)(N(C)C)=O)C.[Li+].CC([N-]C(C)C)C.Cl[CH:38]([C:40]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[N:43]=[CH:42][CH:41]=1)[CH3:39]>C1COCC1>[C:7](=[N:8][CH:9]([CH:38]([C:40]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[N:43]=[CH:42][CH:41]=1)[CH3:39])[C:10]#[N:11])([C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1
参加物反応条件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 12679HexamethylphosphoramideHCID 612957[(Diphenylmethylene)amino]acetonitrileHCID 2724682Lithium diisopropylamideHCID 141713954-(1-Chloroethyl)quinoline

生成物 1

HCID 234992012-(Benzhydrylideneamino)-3-quinolin-4-yl-butyronitrile収率 86%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
-78 °C

実験手順

To N-(Diphenylmethylene)aminoacetonitrile (2.26 g, 10.2 mmol) in 10 ml of anhydrous THF and HMPA (2.17 ml, 12.14 mmol), at −78° C. LDA (2.0 M, 6.0 ml, 12.14 mmol) was added dropwise over a period of 5 minutes. The color of solution turns from coloress to yellow to dark brown. It was then stirred at −78° C. for one hour. Then 4-(1-Chloroethyl)-quinoline (1.79 g, 9.34 mmol), was added dropwise and the reaction mixture was slowly brought to room temperature over a period of five minutes, quenched by addition of ice and partitioned between EtOAc (20 ml) and water (5 ml). The organic layer was dried over sodium sulfate, filtered, concentrated and column purified (hexanes:EtOAc; 3.5:1.5) to give 3.0 g (86%) of the product as a syrup which was used as such for the subsequent step.

後処理

  1. customat −78° C
  2. waitthe reaction mixture was slowly brought to room temperature over a period of five minutes
  3. customquenched by addition of ice
  4. custompartitioned between EtOAc (20 ml) and water (5 ml)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customcolumn purified (hexanes:EtOAc; 3.5:1.5)

出典と根拠

ORDレコード
ord-3b8dfc750974401f910f454705b8ccdc
出典データセット
uspto-grants-2001_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06294566B1

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート