p-Toluenesulfonic acid → 3-Amino-1-(alpha-methyl-3,4-dichlorobenzyl)-pyrazol-5-one

HRID 1679756

Reaktionsgleichung

Reaktionsgleichung von HRID 1679756
[CH3:1][CH:2]([NH:11][NH2:12])[C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[C:5]([Cl:10])[CH:4]=1.C([O:15][C:16](=O)[CH:17]=[C:18]([NH2:22])OCC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C.C(Cl)Cl>[NH2:22][C:18]1[NH:12][N:11]([CH:2]([CH3:1])[C:3]2[CH:8]=[CH:7][C:6]([Cl:9])=[C:5]([Cl:10])[CH:4]=2)[C:16](=[O:15])[CH:17]=1

Komponenten

6

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 278451HCID 278451, VerbindungHCID 3016950(1-(3,4-Dichlorophenyl)ethyl)hydrazine

Produkt 1

HCID 141513883-Amino-1-(alpha-methyl-3,4-dichlorobenzyl)-pyrazol-5-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

41 g of α-methyl-3,4-dichlorobenzylhydrazine, dissolved in absolute ethanol, were added dropwise to a solution of 31.8 g of β-amino-β-ethoxyacrylic acid ethyl ester and 1.5 g of p-toluenesulphonic acid in 150 ml of ethanol at room temperature under nitrogen gas. After stirring for 2 hours and standing overnight, the reaction solution was concentrated as far as possible on a rotary evaporator. The residue which remained was dissolved in 2 N sodium hydroxide solution. Any unconverted starting products or by-products were extracted with ether. The aqueous phase was then brought to pH 5 with acetic acid. The oil thereby produced was taken up in methylene chloride and the organic phase was dried over Na2SO4. After evaporating off the solvent, the reaction product crystallized out. It was recrystallized from methanol. Melting point 127°-129° C; yield 21 g (38.5% of theory).

Aufarbeitung

  1. waitstanding overnight
  2. concentrationthe reaction solution was concentrated as far as
  3. custompossible on a rotary evaporator
  4. dissolutionThe residue which remained was dissolved in 2 N sodium hydroxide solution
  5. extractionwere extracted with ether
  6. customThe oil thereby produced
  7. dry with materialthe organic phase was dried over Na2SO4
  8. customAfter evaporating off the solvent
  9. customthe reaction product crystallized out
  10. customIt was recrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-80e60b2a22f14e97a0d3b79f3f4fd89b
Quelldatensatz
uspto-grants-1978_03
Patentnummer
US04081596

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