Ethanol → HCID 178424609, compound

HRID 2183547Notes

Reaction equation

HRID 2183547 reaction equation
[C:1]([O:7]C)(=O)[CH2:2][C:3]([CH3:5])=O.[CH3:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[C:11]=1[C:18]1[CH:22]=[N:21][NH:20][C:19]=1[NH2:23].C(O)C>C(O)(=O)C>[CH3:5][C:3]1[NH:23][C:19]2[N:20]([N:21]=[CH:22][C:18]=2[C:11]2[C:12]([CH3:17])=[CH:13][C:14]([CH3:16])=[CH:15][C:10]=2[CH3:9])[C:1](=[O:7])[CH:2]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 7757Methyl acetoacetateHCID 224743864-(2,4,6-Trimethyl-phenyl)-2H-pyrazol-3-ylamine

Product 1

HCID 178424609HCID 178424609, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Methyl acetoacetate (0.7 ml) was added to a solution of 4-(2,4,6-Trimethyl-phenyl)-2H-pyrazol-3-ylamine (1.120 g, 5.57 mmol) in 5 ml of acetic acid and the resulting mixture was heated at reflux for two days. Reaction mixture cooled and a white solid formed. Ethanol (6 ml) was added and stirred at room temperature overnight, filtered to give white solid which was recrystallized from ethanol to give 673 mg(45.2%) of the title compound as white crystals. 1H NMR (DMSO-d6) ä 11.9(s, 1H), 7.7(s, 1H), 6.95(s, 2H), 5.55(s, 1H), 2.25(s, 3H), 2.20(s, 3H), 2.0(s, 6H)ppm.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for two days
  3. customReaction mixture
  4. temperaturecooled
  5. customa white solid formed
  6. filtrationfiltered
  7. customto give white solid which
  8. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-e2e79c5a7f4844c6914d6c44d56dd0cf
Source dataset
uspto-grants-2005_05
Patent number
US06900217B2

Reaction notes

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