Trifluoroacetic acid → HCID 66625887, compound

HRID 1663275Notes

Reaction equation

HRID 1663275 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]#[N:8].[CH2:9]([N:11]([CH2:19][CH3:20])[C:12]1[S:16][C:15]([CH:17]=O)=[CH:14][CH:13]=1)[CH3:10].C(O)(C(F)(F)F)=O>C(O)(C)C>[CH2:19]([N:11]([CH2:9][CH3:10])[C:12]1[S:16][C:15]([CH:17]=[N:1][C:2]2[S:3][CH:4]=[CH:5][C:6]=2[C:7]#[N:8])=[CH:14][CH:13]=1)[CH3:20]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7366072-Aminothiophene-3-carbonitrileHCID 153969095-(Diethylamino)thiophene-2-carbaldehyde

Product 1

HCID 66625887HCID 66625887, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In a round bottom flask (50 mL), 30 mg of 2-amino-thiophene-3-carbonitrile was added to 20 mL isopropanol to which was further added 5-diethylamino-thiophene-2-carbaldehyde (48 mg) and a catalytic amount of TFA. The mixture was refluxed for 3 hours. Complete removal of the solvent leads to an orange oil which was purified by flash chromatography (SiO2). The title compound was isolated as an orange solid (63%). 1H-NMR (300 MHz, [D] acetone): δ=8.44 (s, 1H), 7.54 (d, 1H, 3J=4.5 Hz), 7.09 (s, 2H), 6.13 (d, 1H, 3J=4.5 Hz), 3.54 (q, 4H, 3J=7.1 Hz), 1.27 (t, 6H, 3J=7.1 Hz). 13C-NMR (300 MHz, [D] acetone): δ=166.1, 153.2, 141.2, 131.9, 127.9, 123.3, 118.8, 116.0, 104.5, 101.5, 48.2, 12.4.

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. customComplete removal of the solvent
  3. customwas purified by flash chromatography (SiO2)

Sources & evidence

ORD record
ord-2643622a29894229bb99250456d82842
Source dataset
uspto-grants-2011_10
Patent number
US08034895B2

Reaction notes

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