Trifluoroacetic acid → HCID 66625227, compound

HRID 1663269Notes

Reaction equation

HRID 1663269 reaction equation
[N+:1]([C:4]1[S:8][C:7]([CH:9]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(O)(C(F)(F)F)=O.[CH2:18]([O:20][C:21]([C:23]1[C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:26]([NH2:33])[S:25][C:24]=1[NH2:34])=[O:22])[CH3:19]>C(O)(C)C>[CH2:18]([O:20][C:21]([C:23]1[C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:26]([N:33]=[CH:9][C:7]2[S:8][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[S:25][C:24]=1[NH2:34])=[O:22])[CH3:19]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 782815-Nitrothiophene-2-carboxaldehydeHCID 840025Diethyl 2,5-diaminothiophene-3,4-dicarboxylate

Product 1

HCID 66625227HCID 66625227, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In a 50 mL round bottom flask, 30 mg of 2,5-diamino-thiophene-3,4-dicarboxylic acid diethyl ester was dissolved in 20 mL of isopropanol. To this solution, 5-nitro-2-thiophenecarboxaldehyde (91 mg) was added with vigorous stirring, followed by the addition of a catalytic amount of TFA. The reaction was refluxed for 30 minutes. The title compound was isolated as a dark black-purple powder (87%) by flash chromatography (SiO2). M.p.: 194°-196° C. 1H-NMR (300 MHz, [D] acetone): δ=8.21 (s, 1H), 8.00 (d, 1H, 3J=4.4 Hz), 7.74 (s, 2H), 7.50 (d, 1H, 3J=4.4 Hz), 4.37 (q, 2H, 3J=7.1 Hz), 4.22 (q, 2H, 3J=7.1 Hz), 1.40 (t, 3H, 3J=7.1 Hz), 1.27 (t, 3H, 3J=7.1 Hz).

Workup

  1. temperatureThe reaction was refluxed for 30 minutes

Sources & evidence

ORD record
ord-f10f42a455234aa5a5be299dc8352583
Source dataset
uspto-grants-2011_10
Patent number
US08034895B2

Reaction notes

Loading…