Malononitrile → HCID 86678962, compound

HRID 2203317Notes

Reaction equation

HRID 2203317 reaction equation
[H-].[Na+].[C:3](#[N:7])[CH2:4][C:5]#[N:6].Br[C:9]([C:15]1[O:16][C:17]([CH3:20])=[CH:18][N:19]=1)([CH3:14])[C:10]([O:12][CH3:13])=[O:11]>CN(C=O)C>[C:5]([CH:4]([C:3]#[N:7])[C:9]([CH3:14])([C:15]1[O:16][C:17]([CH3:20])=[CH:18][N:19]=1)[C:10]([O:12][CH3:13])=[O:11])#[N:6]

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 24758Sodium hydrideHCID 67993023HCID 67993023, compound

Product 1

HCID 86678962HCID 86678962, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To NaH (60%, 0.085 g, 2.1 mmol) in 5 mL of DMF at 0° C. was added dropwise malononitrile (0.141 g, 2.13 mmol) in 3 mL of DMF. After stirring at room temperature for 15 minutes, the intermediate from Step C in 5 mL of DMF was added. After stirring overnight the reaction mixture was quenched with saturated aqueous NH4Cl. The solution was extracted with EtOAc, dried with MgSO4, and concentrated. The residue was purified by silica gel chromatography using a hexanes/EtOAc gradient to give the indicated compound (a pale yellow oil). 1H NMR (CDCl3, 500 MHz) δ 6.82 (1H, s), 4.86 (1H, s), 3.87 (3H, s), 2.38 (3H, s), 2.05 (3H, s).

Workup

  1. stirringAfter stirring overnight the reaction mixture
  2. customwas quenched with saturated aqueous NH4Cl
  3. extractionThe solution was extracted with EtOAc
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography
  7. customto give the indicated compound (a pale yellow oil)

Sources & evidence

ORD record
ord-566dfcd24b284beabd5c427874541076
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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