Ammonium Acetate → 2-[4-[6-(4-dibutylamino-2-methoxyphenyl)-1,3,5-hexatrienyl]-3-cyano-5,5-dimethyl-2(5H)-furanylidene]propanedinitrile

HRID 85282Notes

Reaction equation

HRID 85282 reaction equation
[CH2:1]([N:5]([CH2:20][CH2:21][CH2:22][CH3:23])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=O)=[C:8]([O:18][CH3:19])[CH:7]=1)[CH2:2][CH2:3][CH3:4].[C:24]([C:26]1[C:27](=[C:34]([C:37]#[N:38])[C:35]#[N:36])[O:28][C:29]([CH3:33])([CH3:32])[C:30]=1[CH3:31])#[N:25].C([O-])(=O)C.[NH4+]>C(O)C.O1CCCC1>[CH2:1]([N:5]([CH2:20][CH2:21][CH2:22][CH3:23])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=[CH:31][C:30]2[C:29]([CH3:32])([CH3:33])[O:28][C:27](=[C:34]([C:35]#[N:36])[C:37]#[N:38])[C:26]=2[C:24]#[N:25])=[C:8]([O:18][CH3:19])[CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 99903452-[3-Cyano-4,5,5-trimethylfuran-2(5H)-ylidene]malononitrileHCID 86667575HCID 86667575, compound

Product 1

HCID 866675742-[4-[6-(4-dibutylamino-2-methoxyphenyl)-1,3,5-hexatrienyl]-3-cyano-5,5-dimethyl-2(5H)-furanylidene]propanedinitrileYield 61.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 3 ml of ethanol and 1 ml of tetrahydrofuran were dissolved 146 mg (0.46 mmol) of 5-(4-dibutylamino-2-methoxyphenyl)-2,4-pentadienal and 101 mg (0.51 mmol) of 2-(3-cyano-4,5,5-trimethyl-2(5H)-furanylidene)propanedinitrile. To this mixture was added 36 mg of ammonium acetate, and the mixture was stirred at room temperature for 19 hours. The precipitate was separated by filtration, washed with ethanol, and purified by silica gel column chromatography to give 140 mg of a dark greenish brown crystal (yield: 60.9%; mp: 156-160° C.)

Workup

  1. customThe precipitate was separated by filtration
  2. washwashed with ethanol
  3. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-fcd8541353364cc3846a5d2620cdc248
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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