Hydrochloric Acid → Ethyl 2-chloro-2-[2-(4-methylphenyl)hydrazono]-acetate

HRID 441847

Reaktionsgleichung

Reaktionsgleichung von HRID 441847
N([O-])=O.[Na+].NC1C=CC(C)=CC=1.Cl.[Cl-].[C:15]1([CH3:23])[CH:20]=[CH:19][C:18]([N+:21]#[N:22])=[CH:17][CH:16]=1.[CH2:24]([O:26][C:27](=[O:30])[CH2:28][Cl:29])[CH3:25].C([O-])(=O)C.[Na+]>C(O)C.O>[CH2:24]([O:26][C:27](=[O:30])[C:28]([Cl:29])=[N:22][NH:21][C:18]1[CH:19]=[CH:20][C:15]([CH3:23])=[CH:16][CH:17]=1)[CH3:25]

Komponenten

9

Edukt 6

HCID 313Hydrochloric AcidHCID 7751Ethyl chloroacetateHCID 7813p-ToluidineHCID 517045Sodium AcetateHCID 103294844-Methylbenzenediazonium chlorideHCID 23668193Sodium Nitrite

Produkt 1

HCID 2761315Ethyl 2-chloro-2-[2-(4-methylphenyl)hydrazono]-acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A solution of 15.2 g. of sodium nitrite in 40 ml. of water is added dropwise to a solution at 0° C. of 21.4 g. of p-toluidine and 400 ml. of 7.5% hydrochloric acid. The suspension of p-toluene diazonium chloride obtained is added dropwise at 5° C. to a mixture consisting of 36.2 g. of 2-chloroacetic acid ethyl ester, 400 ml. of 50% ethanol and 164 g. of sodium acetate. The mixture then is stirred for three hours at 20° C. and extracted with ethyl acetate. The organic phase is concentrated and the residue is treated with petroleum ether. 41 g. of 2-chloro-2-(4-methyl-phenylhydrazono)-acetic acid ethyl ester with a melting point of 100°-101° C., is obtained.

Aufarbeitung

  1. customobtained
  2. additionis added dropwise at 5° C. to a mixture
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic phase is concentrated
  5. additionthe residue is treated with petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-86743dd85e524566adcb5331ae6d5a9e
Quelldatensatz
uspto-grants-1977_08
Patentnummer
US04042706

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