Acetonitrile → HCID 87508268, compound

HRID 1047872Notes

Reaction equation

HRID 1047872 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]=[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]

Participants

6

Reactant 4

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

Product 1

HCID 87508268HCID 87508268, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst

Conditions

Temperature
80 °C

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-70eaa245bb7e4c2dba55b25f5bc813ce
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

Loading…