Trifluoroacetic acid → HCID 66625538, compound

HRID 1663283Notes

Reaction equation

HRID 1663283 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[S:10][C:9]([CH:11]=O)=[CH:8][CH:7]=1.[NH2:13][C:14]1[S:15][C:16]([NH2:29])=[C:17]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:18]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20].C(O)(C(F)(F)F)=O>C(O)(C)C>[CH2:22]([O:21][C:19]([C:18]1[C:17]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:16]([N:29]=[CH:11][C:9]2[S:10][C:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)=[CH:7][CH:8]=2)[S:15][C:14]=1[NH2:13])=[O:20])[CH3:23]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 364428[2,2'-Bithiophene]-5-carboxaldehydeHCID 840025Diethyl 2,5-diaminothiophene-3,4-dicarboxylate

Product 1

HCID 66625538HCID 66625538, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

5-(Thiophen-2-yl)thiophene-2-carbaldehyde (40 mg, 0.25 mmol) was added to diethyl 2,5-diaminothiophene-3,4-dicarboxylate (30 mg, 0.25 mmol) in isopropanol and refluxed for five hours after the addition of a catalytic amount of TFA. The solvent was removed and the title product was isolated as a yellow solid after purification by flash chromatography (42 mg, 64%). 1H-NMR (300 MHz, [D] DMSO): δ=8.19 (s, 1H), 7.89 (s, 2H), 7.58 (d, 1H, 3J=5.2 Hz), 7.50 (d, 1H, 3J=3.9 Hz) 7.41 (d, 1H, 3J=3.6 Hz), 7.34 (d, 1H, 3J=3.9 Hz), 7.11 (t, 1H, J=3.6 Hz), 4.25 (q, 2H, 3J=7.1 Hz), 4.12 (q, 2H, 3J=7.2 Hz), 1.31 (t, 3H, 3J=7.2 Hz), 1.19 (t, 3H, 3J=7.0 Hz). 13C-NMR (60 MHz, [D] acetone): δ=165.5, 164.8, 161.7, 146.1, 142.3, 141.9, 137.7, 137.6, 133.5, 133.4, 131.1, 129.2, 126.9, 125.8, 125.3, 61.5, 60.5, 14.8, 14.6. EI-MS: m/z 434.9 ([M]+, 96%).

Workup

  1. temperaturerefluxed for five hours
  2. customThe solvent was removed

Sources & evidence

ORD record
ord-dec664ead91648489bfc04fc74b5281f
Source dataset
uspto-grants-2011_10
Patent number
US08034895B2

Reaction notes

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