Trifluoroacetic acid → HCID 58036016, compound

HRID 1663279Notes

Reaction equation

HRID 1663279 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[NH2:8][C:9]1[CH:21]=[CH:20][C:19]2[C:18]3[C:13](=[CH:14][C:15]([NH2:22])=[CH:16][CH:17]=3)[CH2:12][C:11]=2[CH:10]=1.[C:23](O)([C:25](F)(F)F)=O>C(O)(C)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[N:8][C:9]1[CH:10]=[C:11]2[C:19]([C:18]3[CH:17]=[CH:16][C:15]([N:22]=[CH:3][C:2]4[S:1][CH:5]=[CH:23][CH:25]=4)=[CH:14][C:13]=3[CH2:12]2)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 73642-ThiophenecarboxaldehydeHCID 106792,7-Diaminofluorene

Product 1

HCID 58036016HCID 58036016, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-Thiophenecarboxaldehyde (131 mg, 1.2 mmol) was added to 2,7-diaminofluorene (100 mg, 0.51 mmol) in anhydrous isopropanol and refluxed for 2 days with a catalytic amount of TFA. The solvent was evaporated and no further purification was required. The title compound was obtained as a yellow powder. (196 mg, mmol, 100%) M.p.: 201° C. 1H-NMR (300 MHz, [D] DMSO): δ=7.88 (d, 2H, 3J=11 Hz), 7.81 (d, 2H, 3J=6.5), 7.69 (d, 2H, 3J=4), 7.50 (s, 2H), 7.30 (d, 2H, 3J=11 Hz), 7.22 (t, 2H, 3J=5.0 Hz), 3.96 (s, 2H). 13C-NMR (300 MHz, [D] DMSO): δ=152.91, 148.43, 142.22, 139.53, 129.74, 127.43, 127.10, 125.82, 123.63, 120.34, 36.52. HR-MS: m/z target 385.08277, measured 385.08388, mass error (ppm) 2.89. C.V. −1.36, −0.77, −0.10, 1.27 V. In 0.1 M TBAPF6 as supporting electrolyte in degassed anhydrous acetonitrile λmax=381 nm. λem=318 and 606 nm. Eg=452 nm, 63.23 Kcal/mol. ΔE=298.8 nm, 95.65 Kcal/mol.

Workup

  1. customThe solvent was evaporated
  2. customno further purification

Sources & evidence

ORD record
ord-81408f9df3734a579897cd3cd090a5b9
Source dataset
uspto-grants-2011_10
Patent number
US08034895B2

Reaction notes

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