Water → 1,1-Dicyanocyclopentane

HRID 2380455Notes

Reaction equation

HRID 2380455 reaction equation
[H-].[Na+].[C:3](#[N:7])[CH2:4][C:5]#[N:6].Br[CH2:9][CH2:10][CH2:11][CH2:12]Br.O>CN(C)C=O>[C:5]([C:4]1([C:3]#[N:7])[CH2:12][CH2:11][CH2:10][CH2:9]1)#[N:6]

Participants

6

Reactant 4

HCID 962WaterHCID 8010MalononitrileHCID 80561,4-DibromobutaneHCID 24758Sodium hydride

Product 1

HCID 151720351,1-Dicyanocyclopentane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (37.8 g; 0.94 moles) was suspended in dimethylformamide (250 mL) under an atmosphere of N2. A solution of malononitrile (30 g; 0.45 moles) and 1,4-dibromobutane 99.7 g; 0.45 moles) in dimethylformamide (150 mL) was added dropwise at such a rate so as not to exceed 30° C. The mixture was stirred for overnight, poured into H2O (500 mL), and then washed with two portions of ethyl ether. The organics were combined, washed with brine, and dried over magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated in vacuo, leaving a bilayered liquid. The lower portion was separated (28.8 g) and identified as the desired product.

Workup

  1. customto exceed 30° C
  2. washwashed with two portions of ethyl ether
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe drying agent was removed by filtration
  6. concentrationthe filtrate was concentrated in vacuo
  7. customleaving a bilayered liquid
  8. customThe lower portion was separated (28.8 g)

Sources & evidence

ORD record
ord-1e72586c169b41738a5c24b60fa9ac33
Source dataset
uspto-grants-1994_11
Patent number
US05366987

Reaction notes

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