Trifluoroacetic acid → HCID 66626031, compound

HRID 1663268Notes

Reaction equation

HRID 1663268 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:9]([NH2:16])[S:8][C:7]=1[NH2:17])=[O:5])[CH3:2].[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[CH:23]=O.FC(F)(F)C(O)=O>C(O)(C)C>[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:9]([N:16]=[CH:23][C:19]2[S:18][CH:22]=[CH:21][CH:20]=2)[S:8][C:7]=1[NH2:17])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 73642-ThiophenecarboxaldehydeHCID 840025Diethyl 2,5-diaminothiophene-3,4-dicarboxylate

Product 1

HCID 66626031HCID 66626031, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In a round bottom flask (50 mL), 2,5-diamino-thiophene-3,4-dicarboxylic acid diethyl ester (50 mg) was added to 20 mL isopropanol to which was added 2-thiophenecarboxaldehyde (24 mg) and a catalytic amount of trifluoroacetic acid (TFA). The mixture was refluxed for 20 hours. Complete removal of the solvent provides an orange solid which was purified by flash chromatography (SiO2), yielding the title compound as an orange solid (81%). M.p.: 114°-116° C. 1H-NMR (300 MHz, [D] acetone): δ=8.24 (s, 1H), 7.63 (d, 1H, 3J=5.0 Hz), 7.52 (dd, 1H, 3J=3.7 Hz and 4J=0.7 Hz), 7.48 (s, 2H), 7.14 (dd, 1H, 3J=5.0 Hz and 3.7 Hz), 4.32 (q, 2H, 3J=7.2 Hz), 4.19 (q, 2H, 3J=7.1 Hz), 1.37 (t, 3H, 3J=7.1 Hz), 1.26 (t, 3H, 3J=7.1 Hz). 13C-NMR (300 MHz, [D] acetone): δ=165.0, 164.3, 161.1, 161.0, 146.1, 143.2, 132.8, 132.1, 130.5, 128.4, 101.8, 61.0, 60.0, 14.3, 14.1.

Workup

  1. temperatureThe mixture was refluxed for 20 hours
  2. customComplete removal of the solvent
  3. customprovides an orange solid which
  4. customwas purified by flash chromatography (SiO2)

Sources & evidence

ORD record
ord-3e57f0fec68446d89f8904372be54a71
Source dataset
uspto-grants-2011_10
Patent number
US08034895B2

Reaction notes

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