Ammonium Acetate → 2-[4-[2-[5-[2-(4-dibutylaminophenyl)vinyl]thiophene-2-yl]vinyl]-3-cyano-5,5-dimethyl-2(5H)-furanylidene]propanedinitrile

HRID 85342Notes

Reaction equation

HRID 85342 reaction equation
[CH2:1]([N:5]([CH2:21][CH2:22][CH2:23][CH3:24])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14]2[S:18][C:17]([CH:19]=O)=[CH:16][CH:15]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[C:25]([C:27]1[C:28](=[C:35]([C:38]#[N:39])[C:36]#[N:37])[O:29][C:30]([CH3:34])([CH3:33])[C:31]=1[CH3:32])#[N:26].C([O-])(=O)C.[NH4+]>C(O)C.O1CCCC1>[CH2:1]([N:5]([CH2:21][CH2:22][CH2:23][CH3:24])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14]2[S:18][C:17]([CH:19]=[CH:32][C:31]3[C:30]([CH3:33])([CH3:34])[O:29][C:28](=[C:35]([C:36]#[N:37])[C:38]#[N:39])[C:27]=3[C:25]#[N:26])=[CH:16][CH:15]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 99903452-[3-Cyano-4,5,5-trimethylfuran-2(5H)-ylidene]malononitrileHCID 765636755-[2-[4-(Dibutylamino)phenyl]vinyl]thiophene-2-carboaldehyde

Product 1

HCID 866676172-[4-[2-[5-[2-(4-dibutylaminophenyl)vinyl]thiophene-2-yl]vinyl]-3-cyano-5,5-dimethyl-2(5H)-furanylidene]propanedinitrileYield 76.1%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

In an ethanol/tetrahydrofuran mixed solvent were dissolved 170 mg (0.50 mmol) of 5-[2-[4-(dibutylamino)phenyl]vinyl]thiophene-2-carboaldehyde and 110 mg (0.55 mmol) of 2-(3-cyano-4,5,5-trimethyl-2(5H)-furanylidene) propanedinitrile. To this mixture, 42 mg of ammonium acetate was added, and the mixture was stirred at room temperature. The solvent was evaporated off. The residue was purified by silica gel column chromatography and washed with ethanol to give 198 mg of a black crystal having amp of 208-209° C. (yield: 76.1%).

Workup

  1. customThe solvent was evaporated off
  2. customThe residue was purified by silica gel column chromatography
  3. washwashed with ethanol

Sources & evidence

ORD record
ord-c4ca73226f7b40f984d1dc3b0f4872f9
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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