Ethanol → HCID 66626477, compound

HRID 1663285Notes

Reaction equation

HRID 1663285 reaction equation
[NH2:1][C:2]1[S:3][C:4]([NH2:13])=[C:5]([C:10]([O-:12])=[O:11])[C:6]=1[C:7]([O-:9])=[O:8].[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[CH:19]=O.[C:21](O)([C:23](F)(F)F)=O.[S:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[C:33]1[S:37][C:36]([CH:38]=O)=[CH:35][CH:34]=1.[CH2:40](O)[CH3:41]>C(O)(C)C>[S:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[C:33]1[S:37][C:36]([CH:38]=[N:1][C:2]2[S:3][C:4]([N:13]=[CH:19][C:15]3[S:14][CH:18]=[CH:17][CH:16]=3)=[C:5]([C:10]([O:12][CH2:21][CH3:23])=[O:11])[C:6]=2[C:7]([O:9][CH2:40][CH3:41])=[O:8])=[CH:35][CH:34]=1

Participants

7

Reactant 5

HCID 702EthanolHCID 6422Trifluoroacetic acid2×HCID 73642-ThiophenecarboxaldehydeHCID 364428[2,2'-Bithiophene]-5-carboxaldehydeHCID 86616915HCID 86616915, compound

Product 1

HCID 66626477HCID 66626477, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

One-step synthesis of the title compound can be achieved by combining 2,5-diaminothiophene-3,4-dicarboxylate (15 mg, 0.5 mmol) with 2-thiophene carboxaldehyde (6.5 mg, 0.6 mmol), followed by refluxing in ethanol for 12 hours in the presence of a catalytic amount of TFA. After removal of the solvent, 5-(thiophen-2-yl)thiophene-2-carbaldehyde (11.3 mg, 0.5 mmol) in isopropanol was added in addition to a catalytic amount of TFA and the solution refluxed for 12 hours. The title compound was isolated as a red powder (20.9 mg, 0.4 mmol, 63%) after flash chromatography (SiO2).

Workup

  1. temperaturethe solution refluxed for 12 hours

Sources & evidence

ORD record
ord-6bd7f2fe446f4937b486b02b4be6fcb2
Source dataset
uspto-grants-2011_10
Patent number
US08034895B2

Reaction notes

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