2,5-Dimethylpyrrole → HCID 178465521, compound

HRID 2361549Notes

Reaction equation

HRID 2361549 reaction equation
C(N([Zr:5]([N:14]([CH3:17])[CH2:15][CH3:16])([N:10]([CH3:13])[CH2:11][CH3:12])N(C)CC)C)C.[CH3:18][C:19]1[NH:20][C:21]([CH3:24])=[CH:22][CH:23]=1>C1(C)C=CC=CC=1>[CH3:18][C:19]1[NH:20][C:21]([CH3:24])=[CH:22][C:23]=1[Zr:5]([C:23]1[CH:22]=[C:21]([CH3:24])[NH:20][C:19]=1[CH3:18])([N:10]([CH2:11][CH3:12])[CH3:13])[N:14]([CH3:17])[CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 122652,5-DimethylpyrroleHCID 178465522HCID 178465522, compound2×

Product 1

HCID 178465521HCID 178465521, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Conditions

Temperature
110 °C

Procedure

In a N2-purged glove box a 100 mL, 3-neck round bottom flask equipped with a magnetic stir bar, thermocouple, and shortpath distillation column was charged with the 3.0 g (9.3 mmol) of tetrakis(ethylmethylamino)zirconium and 20 mL of anhydrous toluene. 1.852 g (19.5 mmol) of 2,5-dimethylpyrrole (Aldrich, pre-dried over 3 A molecular sieves for 24 hours) were dissolved in 20 mL of anhydrous toluene and the solution was added to the toluene solution of tetrakis(ethylmethylamino)zirconium at room temperature during ˜5 min. The reaction was agitated for 1 hour and heated to 110° C. under nitrogen flow. Most of toluene was distilled out under ambient pressure along with the reaction by-product, ethylmethylamine. Remaining toluene and 2,5-dimethylpyrrole were removed under vacuum (100 mtorr) at 80° C. Crude product was purified by sublimation to isolate 2.51 g of bis(2,5-dimethyl-pyrrolyl)bis(ethylmethylamino)zirconium, light yellow solid, mp ˜95° C., 68% purified yield. 1H-NMR (500 MHz, C6D5CD3) δ (ppm): 6.08 (s, 4H), 3.12 (q, 4H), 2.90 (s, 6 H), 2.12 (s, 12 H), 0.88 (t, 6H).

Workup

  1. customIn a N2-purged glove box a 100 mL, 3-neck round bottom flask
  2. customequipped with a magnetic stir bar
  3. distillationthermocouple, and shortpath distillation column
  4. distillationMost of toluene was distilled out under ambient pressure along with the reaction by-product, ethylmethylamine
  5. customRemaining toluene and 2,5-dimethylpyrrole were removed under vacuum (100 mtorr) at 80° C
  6. customCrude product was purified by sublimation

Sources & evidence

ORD record
ord-f5b24c1ab809402289af723b83c04498
Source dataset
uspto-grants-2014_04
Patent number
US08691710B2

Reaction notes

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