2,2-Dimethyl-1,3-dioxane-4,6-dione → 3-(2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)amino-4-carbethoxy-pyrazole

HRID 1026901Notes

Reaction equation

HRID 1026901 reaction equation
[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])[O:3]1.[CH:11](OCC)(OCC)OCC.[NH2:21][C:22]1[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][NH:24][N:23]=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[C:6](=[CH:11][NH:21][C:22]2[NH:23][N:24]=[CH:25][C:26]=2[C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:4](=[O:5])[O:3]1

Participants

5

Reactant 3

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 31214Ethyl orthoformateHCID 178469928HCID 178469928, compound

Product 1

HCID 5407593-(2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)amino-4-carbethoxy-pyrazoleYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Meldrum's acid (15.3 g, 106 mmol) was dissolved in toluene (450 mL), triethyl orthoformate (17.6 mL, 106 mmol) was added, and the mixture was heated under reflux for 2 hr. The reaction mixture was allowed to cool to room temperature, ethyl 3-amino-4-pyrazolecarboxylate (15 g, 96.7 mmol) was added, and the mixture was heated under reflux for 3 hr. The reaction mixture was allowed to cool to room temperature, and stirred at room temperature for 10 hr. The precipitated crystals were collected by filtration, washed with diisopropylether (100 mL), and dried under reduced pressure at 40° C. overnight to give the title compound (26.3 g, 88%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hr
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 3 hr
  5. temperatureto cool to room temperature
  6. filtrationThe precipitated crystals were collected by filtration
  7. washwashed with diisopropylether (100 mL)
  8. customdried under reduced pressure at 40° C. overnight

Sources & evidence

ORD record
ord-1320916e2995492a9e0c9bc515a40fab
Source dataset
uspto-grants-2014_05
Patent number
US08729264B2

Reaction notes

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