Sodium Acetate → HCID 54311389, compound

HRID 1657345Notes

Reaction equation

HRID 1657345 reaction equation
Cl.C([C:4](=[NH:11])[CH2:5][C:6](OCC)=[O:7])C.[Cl:12][C:13]1[CH:18]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[CH:16]=[C:15]([Cl:23])[C:14]=1[NH:24][NH2:25].C([O-])(=O)C.[Na+].[Na]>CO.O.C(O)(=O)C>[Cl:12][C:13]1[CH:18]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[CH:16]=[C:15]([Cl:23])[C:14]=1[N:24]1[C:6](=[O:7])[CH:5]=[C:4]([NH2:11])[NH:25]1

Participants

8

Reactant 4

HCID 517045Sodium AcetateHCID 5360545SodiumHCID 21532817HCID 21532817, compoundHCID 54242666HCID 54242666, compound2×

Product 1

HCID 54311389HCID 54311389, compoundYield 54.5%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 27.5 g of ethyl β-ethyl-β-iminopropionate hydrochloride, 30 g of 2,6 -dichloro-4-methoxycarbonylphenylhydrazine [Intermediate (h) as in Method (a) in Syntheses Example 1-(1)] and 11.5 g of anhydrous sodium acetate in 100 ml of methanol as stirred at room temperature for 2 hours. A solution containing 7 g of metallic sodium dissolved in 70 ml of methanol was added dropwise to the mixture, and the mixture was further stirred at room temperature for 2 hours. After adding 60 ml of acetic acid, the reaction mixture was poured into 1 liter of water. The crystals formed were collected and recrystallized from acetonitrile to obtain 21 g of 1-(2,6 -dichloro-4-methoxycarbonylphenyl)-3-amino-5-pyrazolone having a melting point of 225°-229°C.

Workup

  1. additionwas added dropwise to the mixture
  2. stirringthe mixture was further stirred at room temperature for 2 hours
  3. customThe crystals formed
  4. customwere collected
  5. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-98a16dd106694d3f893d835cdf32afbb
Source dataset
uspto-grants-1976_06
Patent number
US03960571

Reaction notes

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