Reaction #1435701

ord-dd590dc6069b484bbd50972ff09490a8

Reaction equation

C1CCNCC1
piperidine
CC1=CC(=C(C#N)C#N)C=C(C(C)(C)C)O1
2-(2-tert-butyl-6-methyl-pyran-4-ylidene)-malononitrile
O=Cc1ccc(-c2ccc(N(c3ccccc3)c3ccccc3)cc2)s1
5-(4-diphenylamino-phenyl)-thiophene-2-carbaldehyde
CC(C)(C)C1=CC(=C(C#N)C#N)C=C(C=Cc2ccc(-c3ccc(N(c4ccccc4)c4ccccc4)cc3)s2)O1
target compound
Yield 50.0%
CC(C)(C)C1=CC(=C(C#N)C#N)C=C(C=Cc2ccc(-c3ccc(N(c4ccccc4)c4ccccc4)cc3)s2)O1
2-(2-tert-butyl-6-{2-[5-(4-diphenylamino-phenyl)-thiophene-2-yl]-vinyl}-pyran-4-ylidene)-malononitrile
Yield 50.0%

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONwas added
  2. 2
    TemperatureThe reaction solution was heated for 24 hours
  3. 3
    Temperaturewhile refluxing
  4. 4
    TemperatureAfter cooling the reaction solution
  5. 5
    Filtrationthe precipitated red solid was filtered
  6. 6
    Otherrecrystallized with ethanol

Procedure

As shown in the following reaction 3, 0.72 g (3.37 mmol) of (2-(2-tert-butyl-6-methyl-pyran-4-ylidene)-malononitrile and 1 g (2.81 mmol) of 5-(4-diphenylamino-phenyl)-thiophene-2-carbaldehyde were added into 50 ml of ethanol, and 0.28 g (3.37 mmol) of piperidine was added thereto. The reaction solution was heated for 24 hours while refluxing. After cooling the reaction solution, the precipitated red solid was filtered, and recrystallized with ethanol to obtain 0.79 g of the target compound (Yield 50%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07211335B2uspto-grants-2007_05