Tetracyanoethylene → 2-Cyano-3-(4-dibutylamino-2-methoxyphenyl)-2-butenedinitrile

HRID 85322

Reaction equation

HRID 85322 reaction equation
[C:1]([C:3]([C:9]#[N:10])=[C:4]([C:7]#[N:8])[C:5]#[N:6])#N.[CH2:11]([N:15]([CH2:24][CH2:25][CH2:26][CH3:27])[C:16]1[CH:21]=[CH:20]C=[C:18]([O:22][CH3:23])[CH:17]=1)[CH2:12][CH2:13][CH3:14]>CN(C)C=O>[C:5]([C:4](=[C:3]([C:1]1[CH:20]=[CH:21][C:16]([N:15]([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:24][CH2:25][CH2:26][CH3:27])=[CH:17][C:18]=1[O:22][CH3:23])[C:9]#[N:10])[C:7]#[N:8])#[N:6]

Participants

4

Reactant 2

HCID 12635TetracyanoethyleneHCID 4068285N,N-Dibutyl-3-methoxybenzenamine

Product 1

HCID 861937742-Cyano-3-(4-dibutylamino-2-methoxyphenyl)-2-butenedinitrileYield 77.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In 8 ml of N,N-dimethylformamide, 0.5 g (3.9 mmol) of tetracyanoethylene was dissolved. With stirring under ice cooling, 0.8 g (3.4 mmol) of dibutyl(3-methoxyphenyl)amine was dissolved in 2 ml of N,N-dimethylformamide and added dropwise. The mixture was stirred for 35 minutes. After the ice bath was removed, the mixture was further stirred for 2 hours. After the reaction mixture was poured into 100 ml of water, extraction with chloroform, washing with a saturated saline solution, drying over anhydrous sodium sulfate, and concentration were performed. The residue was purified by silica gel column chromatography and washed with hexane to give 0.88 g of a black crystal having a mp of 86° C. (yield: 77.2%).

Workup

  1. additionadded dropwise
  2. stirringThe mixture was stirred for 35 minutes
  3. customAfter the ice bath was removed
  4. stirringthe mixture was further stirred for 2 hours
  5. additionAfter the reaction mixture was poured into 100 ml of water, extraction with chloroform
  6. washwashing with a saturated saline solution
  7. dry with materialdrying over anhydrous sodium sulfate, and concentration
  8. customThe residue was purified by silica gel column chromatography
  9. washwashed with hexane

Sources & evidence

ORD record
ord-392e4ffe9a4b4b3cbb42e9ad5c532ef5
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Linked notes

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