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

HRID 1597365
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HRID 1597365 반응식
[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
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참가 물질

6

반응물 4

HCID 12679HexamethylphosphoramideHCID 612957[(Diphenylmethylene)amino]acetonitrileHCID 2724682Lithium diisopropylamideHCID 141713954-(1-Chloroethyl)quinoline

생성물 1

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

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
-78 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3b8dfc750974401f910f454705b8ccdc
출처 데이터셋
uspto-grants-2001_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06294566B1

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