Trifluoroacetic acid → HCID 66625808, compound

HRID 1663273Notes

Reaction equation

HRID 1663273 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]#[N:8].[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[CH:14]=O.C(O)(C(F)(F)F)=O>C(O)(C)C>[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[CH:14]=[N:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]#[N:8]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 73642-ThiophenecarboxaldehydeHCID 7366072-Aminothiophene-3-carbonitrile

Product 1

HCID 66625808HCID 66625808, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-Amino-thiophene-3-carbonitrile (50 mg) and thiophene-2-carboxaldehyde (54 mg) were mixed in isopropanol with TFA and refluxed for 20 hours. The reaction was then purified by flash chromatography, resulting in 61 mg (70%) of the title compound as an orange solid. M.p. 58°-60° C. 1H-NMR (300 MHz, [D] acetone): δ=8.49 (s, 1H), 7.90 (d, 1H, 3J=5.0 Hz), 7.82 (dd, 1H, 3J=3.7 Hz and 1.0 Hz), 7.42 (d, 1H, 3J=5.7 Hz), 7.27 (m, 2H, 3J=5.6 Hz). 13C-NMR (300 MHz, [D] acetone): δ=163.4, 155.4, 141.8, 136.2, 133.9, 129.0, 128.1, 122.5, 114.6, 105.8.

Workup

  1. temperaturerefluxed for 20 hours
  2. customThe reaction was then purified by flash chromatography

Sources & evidence

ORD record
ord-25f9de83a60d4302b2fd8d60924d0570
Source dataset
uspto-grants-2011_10
Patent number
US08034895B2

Reaction notes

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