Acetic Acid → HCID 54573988, compound

HRID 1657344Notes

Reaction equation

HRID 1657344 reaction equation
Cl.[CH2:2]([O:4][C:5](=N)[CH2:6][C:7](OCC)=[O:8])[CH3:3].[Cl:13][C:14]1[CH:19]=[C:18]([C:20]([O:22][CH3:23])=[O:21])[CH:17]=[C:16]([Cl:24])[C:15]=1[NH:25][NH2:26].[Na].C(O)(=O)C>CO.O>[Cl:13][C:14]1[CH:19]=[C:18]([C:20]([O:22][CH3:23])=[O:21])[CH:17]=[C:16]([Cl:24])[C:15]=1[N:25]1[C:7](=[O:8])[CH:6]=[C:5]([O:4][CH2:2][CH3:3])[NH:26]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 75345Ethyl 3-ethoxy-3-iminopropionate hydrochlorideHCID 5360545SodiumHCID 54242666HCID 54242666, compound2×

Product 1

HCID 54573988HCID 54573988, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

Preparation using the method described in U.S. Pat. No. 3,615,506. A mixture of 11 g of ethyl β-ethoxy-β-iminopropionate hydrochloride and 12 g of 2,6 -dichloro-4-methoxycarbonylphenylhydrazine [Intermediate (h) used in Method (a) above] in 100 ml of methanol was stirred at room temperature for 1 hour. A solution containing 3g of metallic sodium dissolved in 50 ml of methanol was added dropwise to the mixture, and the mixture was further stirred at room temperature (about 20°-30°C) for 1 hour. After adding 15 ml of acetic acid, the reaction mixture was poured into 500 ml of water. The cyrstals formed were collected and recrystallized from methanol to obtain 11 g of 1-(2,6 -dichloro-4-methoxycarbonylphenyl)-3-ethoxy-5-pyrazolone having a melting point of 101°-102.5°C. A mixture of 8 g of the 3-ethoxy-5-pyrazolone compound and 4 g of 2,4 -dichloroaniline was heated to 140° C to form a uniform melt and after adding 1.4 g of methanesulfonic acid to the melt, the reaction was carried out at 140°-150°C for 3 hours with stirring while distilling off the ethanol formed. The reaction mixture was allowed to cool to 100°C and after adding 10 ml of methanol to dissolve the solid, the mixture was allowed to cool to room temperature to form cyrstals which were collected and recrystallized from methanol to obtain the desired compound. The melting point of the product was 132°-135°C and no lowering of the melting point was observed when it was melted together with 1-(2,6 -dichloro-4-methoxycarbonylphenyl)-3-(2,4 -dichloroanilino)-5-pyrazolone prepared by Method (a). The infrared spectra of both compounds were completely identical.

Workup

  1. customPreparation
  2. additionwas added dropwise to the mixture
  3. stirringthe mixture was further stirred at room temperature (about 20°-30°C) for 1 hour
  4. customThe cyrstals formed
  5. customwere collected
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-df7a5561f0df491e88f4b660f6f438dd
Source dataset
uspto-grants-1976_06
Patent number
US03960571

Reaction notes

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