Acetonitrile → HCID 87507794, compound

HRID 1047876Notes

Reaction equation

HRID 1047876 reaction equation
[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]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[CH2:24]Br.[C:26](#[N:28])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]=[CH:21][C:20]=2[Cl:23])[CH:24]1[N+:28]#[C-:26])=[O:5])[CH3:8]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 533707Ethyl isocyanoacetateHCID 150082261,2-Bis(bromomethyl)-4-chlorobenzene

Product 1

HCID 87507794HCID 87507794, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl isocyanoacetate (3.85 mL, 35.0 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-chlorobenzene (10.4 g, 35 mmol). The resulting heterogeneous mixture is stirred at 80° C. overnight. The reaction mixture is cooled 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 a colorless oil (5.06 g, 58%).

Workup

  1. temperatureThe reaction mixture is cooled 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)

Sources & evidence

ORD record
ord-a1715746e4744d7686395dbd5a1d295d
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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