Dabco → HCID 66625913, compound

HRID 1663270Notes

Reaction equation

HRID 1663270 reaction equation
N12CCN(CC1)CC2.[CH2:9]([N:11]([CH2:19][CH3:20])[C:12]1[S:16][C:15]([CH:17]=O)=[CH:14][CH:13]=1)[CH3:10].[CH2:21]([O:23][C:24]([C:26]1[C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[C:29]([NH2:36])[S:28][C:27]=1[NH2:37])=[O:25])[CH3:22]>C1(C)C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[CH2:21]([O:23][C:24]([C:26]1[C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[C:29]([N:36]=[CH:17][C:15]2[S:16][C:12]([N:11]([CH2:19][CH3:20])[CH2:9][CH3:10])=[CH:13][CH:14]=2)[S:28][C:27]=1[NH2:37])=[O:25])[CH3:22]

Participants

6

Reactant 3

HCID 9237DabcoHCID 840025Diethyl 2,5-diaminothiophene-3,4-dicarboxylateHCID 153969095-(Diethylamino)thiophene-2-carbaldehyde

Product 1

HCID 66625913HCID 66625913, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent2×

Procedure

In a 50 mL round bottom flask, 67 mg of 2,5-diamino-thiophene-3,4-dicarboxylic acid diethyl ester was dissolved in 20 mL of anhydrous toluene to which was subsequently added 1,4-diazabicyclo[2.2.2]octane (DABCO, 32 mg), 286 μL of titanium(IV) chloride, 1.0M solution in toluene at 0° C. and 5-diethylamino-thiophene-2-carbaldehyde (52 mg). The mixture was refluxed for two hours and the solvent removed. Purification by flash chromatography (SiO2) yielded the title product as a yellow-orange solid (67%). 1H-NMR (300 MHz, [D] acetone): δ=7.96 (s, 1H), 7.23 (s, 2H), 7.21 (d, 1H, 3J=4.4 Hz), 5.93 (d, 1H, 3J=4.2 Hz), 4.27 (q, 2H, 3J=7.2 Hz), 4.17 (q, 2H, 3J=7.1 Hz), 3.43 (q, 4H, 3J=7.1 Hz), 1.35 (t, 3H, 3J=7.1 Hz), 1.24 (t, 3H, 3J=7.1 Hz), 1.21 (t, 3H, 3J=7.1 Hz). 13C-NMR (300 MHz, [D] acetone): δ=164.5, 162.3, 159.3, 146.9, 135.7, 125.5, 124.5, 102.2, 101.7, 60.7, 59.7, 47.3, 14.2, 14.1, 12.0.

Workup

  1. customat 0° C.
  2. temperatureThe mixture was refluxed for two hours
  3. customthe solvent removed
  4. customPurification by flash chromatography (SiO2)

Sources & evidence

ORD record
ord-45a831f8cd40486fa58391636e0857e6
Source dataset
uspto-grants-2011_10
Patent number
US08034895B2

Reaction notes

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