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

HRID 429040Notes

Reaction equation

HRID 429040 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][CH3:8])[N:5]=[CH:4][CH:3]=1.C(O[CH:12]=[C:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])C>>[CH2:17]([O:16][C:14](=[O:15])[C:13](=[CH:12][NH:1][C:2]1[N:6]([CH2:7][CH3:8])[N:5]=[CH:4][CH:3]=1)[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH3:18]

Participants

3

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

Procedure

A neat solution of 5-amino-1-ethylpyrazole (20.0 g, 180 mmol) and diethyl ethoxymethylenemalonate (42.8 g, 198 mmol) was heated at 120° C. for 5 h. This material was used directly without further purification. If needed, the product can be distilled at 154-160° C. (0.1 mm Hg) to afford the title compound as a liquid which solidified to afford the title compound as a pale colored solid: mp 50-53° C.

Workup

  1. customThis material was used directly without further purification
  2. distillationthe product can be distilled at 154-160° C. (0.1 mm Hg)

Sources & evidence

ORD record
ord-5bc8529a027f4e76a32b0e6b6f4bc2dd
Source dataset
uspto-grants-2001_11
Patent number
US06316438B1

Reaction notes

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