Diethyl (ethoxymethylene)malonate → HCID 10015075, compound

HRID 1507890Notes

Reaction equation

HRID 1507890 reaction equation
[N:1]1([NH2:6])[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH2:7]([O:9][C:10](=[O:21])[C:11](=[CH:17]OCC)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH3:8]>>[N:1]1([NH:6][CH:17]=[C:11]([C:10]([O:9][CH2:7][CH3:8])=[O:21])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:4][CH:3]=[CH:2]1

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 1365891-Aminopyrrole

Product 1

HCID 10015075HCID 10015075, compoundYield 85,888%

Conditions

Temperature
125 °C

Procedure

A round bottom flask was charged with 1H-pyrrole-1-amine (1 g, 0.012 mmol) and diethyl-2-(ethoxymethylene)malonate (3.16 g, 0.014 mmol) and the flask was equipped with a short path distillation condenser. The mixture was heated to 125° C. for 4 hr while collecting the ethanol distillate. After the reaction was complete as determined by TLC, the mixture was cooled to rt and hexanes was added to give a slurry. The mixture was filtered and the resulting solid was rinsed with additional hexanes and was dried to afford 2.6 g (85%) of a solid as the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm: 1.18-1.22 (m, 6H), 4.06-4.17 (m, 4H), 6.06 (t, J=2.4 Hz, 2H), 6.98 (t, J=1.6, 2.4 Hz, 2H), 7.84 (d, J=11.2 Hz, 1H), 11.24 (d, J=10.8 Hz, 1H). LCMS (Condition D): m/z 253 +ve.

Workup

  1. customthe flask was equipped with a short path distillation condenser
  2. distillationwhile collecting the ethanol distillate
  3. temperaturethe mixture was cooled to rt
  4. additionhexanes was added
  5. customto give a slurry
  6. filtrationThe mixture was filtered
  7. washthe resulting solid was rinsed with additional hexanes
  8. customwas dried

Sources & evidence

ORD record
ord-d49fde6af304407685e343759f3fa140
Source dataset
uspto-grants-2015_12
Patent number
US09221826B2

Reaction notes

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