Trifluoroacetic acid → HCID 66625149, compound

HRID 1663274Notes

Reaction equation

HRID 1663274 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]#[N:8].[N+:9]([C:12]1[S:16][C:15]([CH:17]=O)=[CH:14][CH:13]=1)([O-:11])=[O:10].C(O)(C(F)(F)F)=O>C(O)(C)C>[N+:9]([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)([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 782815-Nitrothiophene-2-carboxaldehydeHCID 7366072-Aminothiophene-3-carbonitrile

Product 1

HCID 66625149HCID 66625149, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-Amino-thiophene-3-carbonitrile (30 mg) and 5-nitro-thiophene-2-carboxaldehyde (41 mg) were mixed in isopropanol with TFA and refluxed for 28 hours. The reaction was then purified by flash chromatography, resulting in 45 mg (71%) of the title compound as an orange powder. M.p.: 192°-194° C. 1H-NMR (300 MHz, [D]acetone): δ=8.98 (s, 1H), 8.12 (d, 1H, 3J=4.3 Hz), 7.85 (d, 1H, 3J=4.3 Hz), 7.61 (d, 1H, 3J=5.7 Hz), 7.38 (d, 1H, 3J=5.7 Hz). 13C-NMR (300 MHz, [D] acetone): δ=161.2, 154.3, 147.3, 133.7, 130.0, 128.6, 125.9, 125.1, 109.5, 108.5.

Workup

  1. temperaturerefluxed for 28 hours
  2. customThe reaction was then purified by flash chromatography

Sources & evidence

ORD record
ord-19aad89fc4b04771a767fdf9a5144c7c
Source dataset
uspto-grants-2011_10
Patent number
US08034895B2

Reaction notes

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