Ammonium Acetate → 2-[4-[2-[4-[2-(4-dibutylamino-2-methoxyphenyl)vinyl]phenyl]vinyl]-3-cyano-5,5-dimethyl-2(5H)-furanylidene]propanedinitrile

HRID 85251Notes

Reaction equation

HRID 85251 reaction equation
[CH2:1]([N:5]([CH2:24][CH2:25][CH2:26][CH3:27])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14]2[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=2)=[C:8]([O:22][CH3:23])[CH:7]=1)[CH2:2][CH2:3][CH3:4].[C:28]([C:30]1[C:31](=[C:38]([C:41]#[N:42])[C:39]#[N:40])[O:32][C:33]([CH3:37])([CH3:36])[C:34]=1[CH3:35])#[N:29].C([O-])(=O)C.[NH4+]>C(O)C.O1CCCC1>[CH2:24]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14]2[CH:21]=[CH:20][C:17]([CH:18]=[CH:35][C:34]3[C:33]([CH3:36])([CH3:37])[O:32][C:31](=[C:38]([C:39]#[N:40])[C:41]#[N:42])[C:30]=3[C:28]#[N:29])=[CH:16][CH:15]=2)=[C:8]([O:22][CH3:23])[CH:7]=1)[CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 99903452-[3-Cyano-4,5,5-trimethylfuran-2(5H)-ylidene]malononitrileHCID 866675494-[2-(4-Dibutylamino-2-methoxyphenyl)vinyl]benzaldehyde

Product 1

HCID 866675502-[4-[2-[4-[2-(4-dibutylamino-2-methoxyphenyl)vinyl]phenyl]vinyl]-3-cyano-5,5-dimethyl-2(5H)-furanylidene]propanedinitrileYield 92.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 15 ml of ethanol and 5 ml of tetrahydrofuran were dissolved 500 mg (1.37 mmol) of 4-[2-(4-dibutylamino-2-methoxyphenyl)vinyl]benzaldehyde and 300 mg (1.51 mmol) of 2-(3-cyano-4,5,5-trimethyl-2(5H)-furanylidene) propanedinitrile. To this mixture was added 106 mg of ammonium acetate, and the mixture was stirred at room temperature for 23 hours. The solvent was evaporated off in a reduced pressure. The residue was washed with ethanol and then purified by silica gel column chromatography. The crystal was washed with ethanol to give 693 mg of a black powder (yield: 92.6%; mp: 258-260° C.)

Workup

  1. customThe solvent was evaporated off in a reduced pressure
  2. washThe residue was washed with ethanol
  3. custompurified by silica gel column chromatography
  4. washThe crystal was washed with ethanol

Sources & evidence

ORD record
ord-1c59827ae4c646e8a7cf6cea46b42a3a
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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