Malononitrile → HCID 86678963, compound

HRID 2203321Notes

Reaction equation

HRID 2203321 reaction equation
[H-].[Na+].[C:3](#[N:7])[CH2:4][C:5]#[N:6].Br[C:9]([C:15]1[N:16]=[C:17]([CH3:20])[O:18][CH: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[N:16]=[C:17]([CH3:20])[O:18][CH:19]=1)[C:10]([O:12][CH3:13])=[O:11])#[N:6]

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 24758Sodium hydrideHCID 67992976HCID 67992976, compound

Product 1

HCID 86678963HCID 86678963, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To NaH (60%, 0.293 g, 7.32 mmol) in 10 mL of DMF at room temperature was added dropwise malononitrile (0.483 g, 7.32 mmol) in 5 mL of DMF. After stirring at room temperature for 15 minutes, the intermediate from Step C (1.82 g, 7.32 mmol) in 10 mL of DMF was added. The resulting mixture was stirred for 2 hours and then quenched with water. The mixture 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 7.66 (1H, s), 4.88 (1H, s), 3.87 (3H, s), 2.49 (3H, s), 1.92 (3H, s). m/z=234 (M+H).

Workup

  1. stirringThe resulting mixture was stirred for 2 hours
  2. customquenched with water
  3. extractionThe mixture 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-0a44864e3bc44124a86302345242c40b
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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