Malononitrile → HCID 88545043, compound

HRID 2203310Notes

Reaction equation

HRID 2203310 reaction equation
[H-].[Na+].[C:3](#[N:7])[CH2:4][C:5]#[N:6].Br[C:9]([C:15]1[CH:20]=[N:19][CH:18]=[CH:17][N:16]=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[CH:20]=[N:19][CH:18]=[CH:17][N:16]=1)[C:10]([O:12][CH3:13])=[O:11])#[N:6]

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 24758Sodium hydrideHCID 67996613HCID 67996613, compound

Product 1

HCID 88545043HCID 88545043, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A DMF (15 mL) solution of sodium hydride (0.38 g, 9.4 mmol, 60%) was added to malononitrile (0.62 g, 9.4 mmol) in DMF (3 mL) at 0° C. After 10 minutes the intermediate from Step C (2.1 g, 8.6 mmol) was added. After stirring for 2 hours at room temperature the reaction was quenched with saturated aqueous NH4Cl. The mixture was extracted with ethyl acetate and the organic layer concentrated. The residue was purified by silica gel chromatography using a hexanes/EtOAc gradient to give the indicated product. 1H NMR δ (ppm) (CHCl3-d): 8.85 (1H, s), 8.65 (1H, d, J=2.6 Hz), 8.58 (1H, s), 5.12 (1H, s), 3.81 (3H, s), 2.09 (3H, s). m/z=231.0 (M+H).

Workup

  1. customwas quenched with saturated aqueous NH4Cl
  2. extractionThe mixture was extracted with ethyl acetate
  3. concentrationthe organic layer concentrated
  4. customThe residue was purified by silica gel chromatography
  5. customto give the indicated product

Sources & evidence

ORD record
ord-b5b2e6b0a77f48e1819bf9d0ecc19a08
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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