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Acetonitrile → HCID 87508268, 화합물

HRID 1047872
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HRID 1047872 반응식
[N+]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[C-].[C:9]([O-])([O-])=O.[K+].[K+].BrC[C:17]1[CH:22]=[C:21]([Cl:23])[C:20]([Cl:24])=[CH:19][C:18]=1[CH2:25]Br.[C:27](#[N:29])C>CCCC[N+](CCCC)(CCCC)CCCC.OS([O-])(=O)=O>[CH2:7]([O:6][C:4]([CH:3]1[CH2:9][C:19]2[C:18](=[CH:17][CH:22]=[C:21]([Cl:23])[C:20]=2[Cl:24])[CH:25]1[N+:29]#[C-:27])=[O:5])[CH3:8]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 2911421,2-Bis(bromomethyl)-4,5-dichlorobenzeneHCID 533707Ethyl isocyanoacetate

생성물 1

HCID 87508268HCID 87508268, 화합물수율 66%

시약·촉매·용매 1

HCID 94433
Tetrabutylammonium hydrogen sulfate
촉매

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온도
80 °C

실험 절차

To a solution of ethyl isocyanoacetate (3.85 mL, 35 mmol) in anhydrous ACN (300 mL) is added finely ground anhydrous K2CO3 (29 g, 210 mmol), TBAHS (tetrabutyl ammonium hydrogen sulfate, 2.34 g, 7 mmol), and 1,2-bis-(bromomethyl)-4,5-dichlorobenzene (11.6 g, 35 mmol). The resulting heterogeneous mixture is stirred at 80° C. overnight. The reaction mixture is cooled down to RT and filtered to remove the unwanted salts. The filtrate is concentrated in vacuo. The residue is purified by flash column chromatography (200 g silica gel; gradient elution: 0-25% EtOAc in heptane) to give a pure product as white powder (6.63 g, 66%).

후처리

  1. temperatureThe reaction mixture is cooled down to RT
  2. filtrationfiltered
  3. customto remove the unwanted salts
  4. concentrationThe filtrate is concentrated in vacuo
  5. customThe residue is purified by flash column chromatography (200 g silica gel; gradient elution: 0-25% EtOAc in heptane)

출처 및 근거

ORD 기록
ord-70eaa245bb7e4c2dba55b25f5bc813ce
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08569535B2

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