Diethyl (ethoxymethylene)malonate → [[(1-Ethyl-3-methyl-5-pyrazolyl)amino]methylene]malonic acid diethyl ester

HRID 329176Notes

Reaction equation

HRID 329176 reaction equation
[CH2:1]([N:3]1[C:7]([NH2:8])=[CH:6][C:5]([CH3:9])=[N:4]1)[CH3:2].[CH2:10]([O:12][C:13](=[O:24])[C:14](=[CH:20]OCC)[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:11]>C(O)C>[CH2:10]([O:12][C:13](=[O:24])[C:14](=[CH:20][NH:8][C:7]1[N:3]([CH2:1][CH3:2])[N:4]=[C:5]([CH3:9])[CH:6]=1)[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:11]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 27683831-Ethyl-3-methyl-1H-pyrazol-5-amine

Product 1

HCID 11380881[[(1-Ethyl-3-methyl-5-pyrazolyl)amino]methylene]malonic acid diethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

12.5 g. of 1-ethyl-3-methyl-5-aminopyrazole (0.1 mol.) and 21.6 g. of ethoxymethylene malonic acid diethyl ester (0.1 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. 0.05 152°-153°) yields 24.0 g. (81.5%) of a quickly crystallizing oil, [[(1-ethyl-3-methyl-5-pyrazolyl)amino]methylene]malonic acid diethyl ester, m.p. 60°-67°. The product, recrystallized from ligroin (90°-100° C), melts at 69°-70°.

Workup

  1. customis removed by means of a water aspirator
  2. distillationVacuum distillation (b.p. 0.05 152°-153°)
  3. customyields 24.0 g
  4. custom(81.5%) of a quickly crystallizing oil, [[(1-ethyl-3-methyl-5-pyrazolyl)amino]methylene]malonic acid diethyl ester, m.p. 60°-67°
  5. customThe product, recrystallized from ligroin (90°-100° C), melts at 69°-70°

Sources & evidence

ORD record
ord-cf3c2a5cb61f4a5cbb7cfb67716669ef
Source dataset
uspto-grants-1977_04
Patent number
US04020072

Reaction notes

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