Diethyl (ethoxymethylene)malonate → HCID 10491075, compound

HRID 2171308Notes

Reaction equation

HRID 2171308 reaction equation
[NH:1]1[C:5]([NH2:6])=[CH:4][CH:3]=[N:2]1.C(O[CH:10]=[C:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])C>>[NH:1]1[C:5]([NH:6][CH:10]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:4][CH:3]=[N:2]1

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 74561Pyrazol-3-ylamine

Product 1

HCID 10491075HCID 10491075, compound

Conditions

Temperature
200 °C

Procedure

A mixture of 1H-pyrazol-5-amine 1 (2 g, 24.1 mmol) and diethyl 2-(ethoxymethylene)malonate (10.4 g, 48.2 mmol) was heated at 200° C. until the starting material was consumed completely. The reaction mixture was allowed to cool to room temperature and EtOH (10 mL) was added. A precipitate formed, which was removed by filtration, washed with EtOH and dried under vacuum to give diethyl 2-((1H-pyrazol-5-ylamino)methylene)malonate; 4.0 g (66%). 1H NMR (300 MHz, CDCl3) δ 10.95 (d, J=13.5 Hz, 1H), 8.60 (d, J=13.8 Hz, 1H), 7.52 (d, J=2.4 Hz, 1H), 6.08 (d, J=2.4 Hz, 1H), 4.30 (q, J=7.2 Hz, 2H), 4.22 (q, J=7.2 Hz, 2H), 1.36 (t, J=7.2 Hz, 3H), 1.31 (t, J=7.2 Hz, 3H).

Workup

  1. customwas consumed completely
  2. temperatureto cool to room temperature
  3. additionEtOH (10 mL) was added
  4. customA precipitate formed
  5. customwhich was removed by filtration
  6. washwashed with EtOH
  7. customdried under vacuum

Sources & evidence

ORD record
ord-f195cb429e8a4c749da5f744f7d41a76
Source dataset
uspto-grants-2015_06
Patent number
US09051324B2

Reaction notes

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