Trifluoroacetic acid → HCID 66625082, compound

HRID 1663286Notes

Reaction equation

HRID 1663286 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:30](O)([C:32](F)(F)F)=O>C(O)(C)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[S:10][C:30]([CH:32]=[N:13][C:14]2[S:15][C:16]([N:29]=[CH:11][C:9]3[S:10][C:6]([C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)=[CH:7][CH:8]=3)=[C:17]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:18]=2[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:8][CH:7]=1

Participants

5

Reactant 3

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

Product 1

HCID 66625082HCID 66625082, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

5-(Thiophen-2-yl)thiophene-2-carbaldehyde (75 mg) was added to diethyl 2,5-diaminothiophene-3,4-dicarboxylate (49 mg) and the solution was refluxed in isopropanol for four hours in the presence of a catalytic amount of TFA. The title compound was isolated as a red powder (58 mg, 50%) following column chromatography. M.p.: 130°-132° C. 1H-NMR (300 MHz, [D] acetone): δ=8.69 (s, 2H), 7.76 (d, 2H, 3J=4.1 Hz), 7.66 (d, 2H, 3J=6.1 Hz), 7.53 (d, 2H, 3J=3.7 Hz), 7.46 (d, 2H, 3J=4.0 Hz), 7.16 (t, 2H, 3J=3.6 Hz), 4.26 (q, 4H, 3J=6). 9 Hz), 1.30 (t, 6H, 3J=7.3 Hz). 13C-NMR (60 MHz, [D] acetone): δ=173.0, 163.0, 152.8, 140.9, 136.4, 131.6, 129.2, 129.0, 127.3, 126.2, 125.2, 123.9, 66.3, 13.8. EI-MS: m/z 610.9 ([M]+, 100%).

Sources & evidence

ORD record
ord-4a922829b5a540fb997eeac9276842c1
Source dataset
uspto-grants-2011_10
Patent number
US08034895B2

Reaction notes

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