Diethyl (ethoxymethylene)malonate → 2-[(2-Benzyl-2H-pyrazol-3-ylamino)-methylene]-malonic acid diethyl ester

HRID 451213Notes

Reaction equation

HRID 451213 reaction equation
[CH2:1]([N:8]1[C:12]([NH2:13])=[CH:11][CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:14]([O:16][C:17](=[O:28])[C:18](=[CH:24]OCC)[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH3:15]>>[CH2:14]([O:16][C:17](=[O:28])[C:18](=[CH:24][NH:13][C:12]1[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[N:9]=[CH:10][CH:11]=1)[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH3:15]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 770611-Benzyl-1H-pyrazol-5-amine

Product 1

HCID 128450792-[(2-Benzyl-2H-pyrazol-3-ylamino)-methylene]-malonic acid diethyl esterYield 75%

Conditions

Temperature
120 °C

Procedure

To 2-benzyl-2H-pyrazol-3-ylamine (5.0 g, 0.0289 mol) was added 2-ethoxymethylene-malonic acid diethyl ester (5.78 mL, 0.0289 mol) and the mixture was heated at 120° C. for 4 hours. After cooling down to RT, the crude mixture was purified by column chromatography (SiO2, EtOAc/Heptane 1/1) to give 7.44 g (75%) of the title compound as a light yellow oil.

Workup

  1. temperatureAfter cooling down to RT
  2. customthe crude mixture was purified by column chromatography (SiO2, EtOAc/Heptane 1/1)

Sources & evidence

ORD record
ord-59b2cae7cdbc4f328c80254e73adc907
Source dataset
uspto-grants-2013_07
Patent number
US08487102B2

Reaction notes

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