Dabco → HCID 66626032, compound

HRID 1663276Notes

Reaction equation

HRID 1663276 reaction equation
[N+:1]([C:4]1[S:8][C:7]([CH:9]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].C1N2CCN(CC2)C1.[CH2:19]([O:21][C:22]([C:24]1[C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:27]([N:34]=CC2SC=CC=2)[S:26][C:25]=1[N:41]=[CH:42][C:43]1[S:44][CH:45]=[CH:46][CH:47]=1)=[O:23])[CH3:20]>C1(C)C=CC=CC=1.Cl[Ti](Cl)(Cl)Cl>[CH2:32]([O:31][C:29]([C:28]1[C:24]([C:22]([O:21][CH2:19][CH3:20])=[O:23])=[C:25]([N:41]=[CH:42][C:43]2[S:44][CH:45]=[CH:46][CH:47]=2)[S:26][C:27]=1[N:34]=[CH:9][C:7]1[S:8][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)=[O:30])[CH3:33]

Participants

6

Reactant 3

HCID 9237DabcoHCID 782815-Nitrothiophene-2-carboxaldehydeHCID 66625194HCID 66625194, compound

Product 1

HCID 66626032HCID 66626032, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent2×

Procedure

5-Nitrothiophene-2-carbaldehyde (9 mg) was mixed in toluene under nitrogen at 0° C. with DABCO (7 mg), TiCl4 in solution in toluene (59 μL) and 2,5-bis-[(thiophen-2-ylmethylene)-amino]-thiophene-3,4-dicarboxylic acid diethyl ester (12 mg). The mixture was refluxed for six hours, concentrated and the product isolated as a red powder after purification by flash chromatography. M.p.: 220°-222° C. 1H-NMR (300 MHz, [D] acetone): δ=8.81 (s, 1H), 8.79 (s, 1H), 8.10 (d, 1H, 3.2 Hz), 7.91 (d, 1H, 3J=4.1 Hz), 7.81 (d, 1H, 2.9 Hz), 7.78 (d, 1H, 3J=4.6 Hz), 7.29 (dd, 1H, 2.7 Hz and 3.8 Hz), 4.38 (q, 2H, 3J=5.3 Hz), 4.32 (q, 2H, 3J=5.3 Hz), 1.41 (t, 3H, 3J=5.3 Hz), 1.36 (t, 3H, 3J=5.3 Hz). 13C-NMR (300 MHz, [D] acetone): δ=176.9, 174.2, 169.1, 166.5, 155.1, 151.7, 146.6, 142.2, 140.9, 136.1, 135.9, 134.0, 132.7, 130.0, 129.0, 127.5, 61.5, 61.3, 14.2, 14.0.

Workup

  1. temperatureThe mixture was refluxed for six hours
  2. concentrationconcentrated
  3. customthe product isolated as a red powder
  4. customafter purification by flash chromatography

Sources & evidence

ORD record
ord-57c204c045744bbd838e803fbaee2fa8
Source dataset
uspto-grants-2011_10
Patent number
US08034895B2

Reaction notes

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