Diethyl (ethoxymethylene)malonate → Diethyl {[(1-ethyl-1H-pyrazol-5-yl)amino]methylene}malonate

HRID 1576082Notes

Reaction equation

HRID 1576082 reaction equation
[CH2:1]([N:3]1[C:7]([NH2:8])=[CH:6][CH:5]=[N:4]1)[CH3:2].[CH2:9]([O:11][C:12](=[O:23])[C:13](=[CH:19]OCC)[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH3:10]>C(O)C>[CH2:9]([O:11][C:12](=[O:23])[C:13](=[CH:19][NH:8][C:7]1[N:3]([CH2:1][CH3:2])[N:4]=[CH:5][CH:6]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH3:10]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 3373101-Ethyl-1H-pyrazol-5-amine

Product 1

HCID 12845080Diethyl {[(1-ethyl-1H-pyrazol-5-yl)amino]methylene}malonate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

245 g of 1-ethyl-5-aminopyrazole (2.2mol) and 476 g of ethoxymethylene malonic acid diethyl ester (2.2 mol) are heated to 120° (bath temperature) for 2 hours with stirring. The ethanol formed by this reaction is removed by means of a water aspirator. Vacuum distillation (b.p.0.1 154°-160°) yields 520 g (84% of theory) of a quickly crystallizing oil of [[(1-ethyl-5-pyrazolyl)amino]methylene]malonic acid diethyl ester, m.p. 50°-53°. The compound is recrystallized from N-hexane, and has a melting point of 55°-57°.

Workup

  1. customis removed by means of a water aspirator
  2. distillationVacuum distillation (b.p.0.1 154°-160°)
  3. customyields 520 g (84% of theory) of
  4. customa quickly crystallizing oil of [[(1-ethyl-5-pyrazolyl)amino]methylene]malonic acid diethyl ester, m.p. 50°-53°
  5. customThe compound is recrystallized from N-hexane

Sources & evidence

ORD record
ord-e3fe18475f774fc9ae8a49e25ba044de
Source dataset
uspto-grants-1976_09
Patent number
US03979399

Reaction notes

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