Acetic Acid → HCID 178469359, compound

HRID 2360675Notes

Reaction equation

HRID 2360675 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][N:3]=1.[Na].[C:9]([O:16][CH2:17][CH3:18])(=[O:15])[C:10](OCC)=O.[C:19](O)(=[O:21])[CH3:20]>Cl>[CH2:17]([O:16][C:9]([C:10]1[C:6]2[C:5]([CH3:7])=[N:4][NH:3][C:2]=2[N:1]=[C:19]([OH:21])[CH:20]=1)=[O:15])[CH3:18]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 86680294HCID 86680294, compound

Product 1

HCID 178469359HCID 178469359, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-amino-5-methylpyrazole (50.0 g), diethyl oxalate sodium salt (127.3 g) and acetic acid (113 mL) in 1N aqueous hydrochloric acid (625 mL) was stirred at 80° C. for 14 h, then refluxed for 3 h, cooled to r.t., and the precipitate formed was filtered by suction filtration and dried in vacuo at 60° C. The crude product was stirred in 500 mL ethyl acetate at r.t. and the solid was filtered off and dried in air. 40.2 g (35%) of the title compound were obtained as pale yellow solid.

Workup

  1. temperaturerefluxed for 3 h
  2. temperaturecooled to r.t.
  3. customthe precipitate formed
  4. filtrationwas filtered by suction filtration
  5. customdried in vacuo at 60° C
  6. stirringThe crude product was stirred in 500 mL ethyl acetate at r.t.
  7. filtrationthe solid was filtered off
  8. customdried in air

Sources & evidence

ORD record
ord-faa584e7be354c82bb4614d517fe9a48
Source dataset
uspto-grants-2014_04
Patent number
US08686150B2

Reaction notes

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