Acetic Acid → HCID 178422355, compound

HRID 1639652Notes

Reaction equation

HRID 1639652 reaction equation
[C:1]([O:7]CC)(=O)[CH2:2][C:3]([CH3:5])=O.C(O)(=O)C.[CH3:14][C:15]1[CH:16]=[C:17]([NH2:20])[NH:18][N:19]=1>COC(C)(C)C>[CH3:14][C:15]1[CH:16]=[C:17]2[NH:20][C:3]([CH3:5])=[CH:2][C:1](=[O:7])[N:18]2[N:19]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8868Ethyl AcetoacetateHCID 178418690HCID 178418690, compound

Product 1

HCID 178422355HCID 178422355, compoundYield 101.9%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

Add ethyl acetoacetate (128 g, 0.98 mol) dropwise to an acetic acid solution (500 mL) of 5-methyl-2H-pyrazol-3-ylamine (100 g, 0.95 mol), keeping the temperature at 25-28° C. Heat the mixture at reflux for 10 h and then cool to room temperature. Add the reaction to tert-butyl methyl ether (5 L) cooled to 5° C., keeping the temperature below 10° C. Stir for 1 h at 5° C., and filter. Dry the resulting material in vacuo overnight to provide a white solid (158 g, 96%).

Workup

  1. customat 25-28° C
  2. temperatureHeat the mixture
  3. temperatureat reflux for 10 h
  4. additionAdd
  5. temperaturecooled to 5° C.
  6. customthe temperature below 10° C
  7. filtrationfilter
  8. customDry the resulting material in vacuo overnight

Sources & evidence

ORD record
ord-6e732b7a64e04967afe6a0e78758dba7
Source dataset
uspto-grants-2012_02
Patent number
US08110580B2

Reaction notes

Loading…