Malononitrile → HCID 59062734, compound

HRID 1611210Notes

Reaction equation

HRID 1611210 reaction equation
[C:1](Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][O:16][CH2:17][C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=O)=[CH:11][CH:10]=1.[C:26](#[N:30])[CH2:27][C:28]#[N:29].C[CH2:32][N:33](CC)[CH2:34]C>C(#N)C.CN(C=O)C.O>[CH3:32][N:33]([CH3:34])/[C:22](/[C:23]1[CH:24]=[CH:25][CH:20]=[CH:18][C:17]=1[O:16][CH2:15][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH3:7])=[CH:14][CH:13]=1)=[CH:21]\[CH:1]=[C:27]([C:26]#[N:30])[C:28]#[N:29]

Participants

8

Reactant 4

HCID 8010MalononitrileHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 22258775HCID 22258775, compound2×

Product 1

HCID 59062734HCID 59062734, compoundYield 27.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 6342AcetonitrileSolvent

Procedure

To a solution of oxalyl chloride (3.63 g, 28.6 mmol) in acetonitrile (5.00 mL) at room temperature was added DMF (5.00 mL). After 10 minutes, a solution of 2-(4-methoxyphenylmethoxy)acetophenone (3.33 g, 13.0 mmol)(starting compound 1D) in DMF (50 mL) was added, and the stirring was continued overnight. To the reaction mixture were added malononitrile (1.03 g, 15.6 mmol) and Et3N (7.25 mL, 52.0 mmol) successively, and the stirring was continued overnight. The reaction mixture was poured into water, and then extracted with ether. The separated organic phase was washed with brine, and dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (CHCl3) to give 2-((2Z)-3-(dimethylamino)-3-{2-[(4-methoxybenzyl)oxy]phenyl}-2-propenylidene)malononitrile (1.27 g yield; 27%).

Workup

  1. waitthe stirring was continued overnight
  2. waitthe stirring was continued overnight
  3. extractionextracted with ether
  4. washThe separated organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (CHCl3)

Sources & evidence

ORD record
ord-27bbcc6ef9084113bacb50dc68cefb2d
Source dataset
uspto-grants-2006_01
Patent number
US06984649B1

Reaction notes

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