Hydrochloric Acid → HCID 22235003, compound

HRID 749539Notes

Reaction equation

HRID 749539 reaction equation
[I:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[H-].[Na+].[F:12][C:13]([F:22])([F:21])[CH2:14][CH2:15][CH:16]([C:19]#[N:20])[C:17]#[N:18].Cl>CN(C)C=O>[I:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][C:16]([CH2:15][CH2:14][C:13]([F:12])([F:21])[F:22])([C:17]#[N:18])[C:19]#[N:20])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 9542584-Iodobenzyl bromideHCID 221857612-(3,3,3-Trifluoropropyl)malononitrile

Product 1

HCID 22235003HCID 22235003, compoundYield 22.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

First, 0.55 g of 4-iodobenzyl bromide was dissolved in 10 ml of N,N-dimethylformamide, to which the suspension of 0.11 g of sodium hydride (60% in oil) and 0.30 g of (3,3,3-trifluoropropyl)malononitrile in 5 ml of N,N-dimethylformamide was added dropwise, while stirring under ice cooling. After stirring for 4 hours at 0° C., 10% hydrochloric acid was added to the reaction mixture at room temperature, which was extracted with ethyl acetate. The organic layer was successively washed with water, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.16 g of 2-(4-iodobenzyl)-2-(3,3,3-trifluoropropyl)malononitrile (the present compound (26)).

Workup

  1. additionwas added dropwise
  2. stirringAfter stirring for 4 hours at 0° C.
  3. extractionwhich was extracted with ethyl acetate
  4. washThe organic layer was successively washed with water
  5. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cec7e3d79eb444efa059ed3cab5c61a5
Source dataset
uspto-grants-2008_07
Patent number
US07402691B2

Reaction notes

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