Malononitrile → HCID 59062734, compound

HRID 2115737Notes

Reaction equation

HRID 2115737 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 adde 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, filtetred 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. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (CHCl3)

Sources & evidence

ORD record
ord-12a2c42ae50e42518d4155343cb7250a
Source dataset
uspto-grants-2008_10
Patent number
US07435743B2

Reaction notes

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