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

HRID 870392

Reaktionsgleichung

Reaktionsgleichung von HRID 870392
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.Cl.[N:11]([O-])=O.[Na+].[CH2:15]([O:17][C:18](=[O:24])[CH:19]([Cl:23])C(C)=O)[CH3:16].C(O[Na])(C)=O>O.CCOC(C)=O>[CH2:15]([O:17][C:18](=[O:24])[C:19]([Cl:23])=[N:11][NH:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH3:16]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 7732P-AnisidineHCID 11858Ethyl 2-chloroacetoacetateHCID 23668193Sodium NitriteHCID 178418247HCID 178418247, Verbindung

Produkt 1

HCID 21829645Ethyl 2-chloro-2-[2-(4-methoxyphenyl)hydrazono]acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel3×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

p-anisidine (31.02 g, 0.252 mol) in 100 ml of H2O is suspended in a 250 ml 4-necked flask equipped with coolant, thermometer, dropping funnel and magnetic stirrer, and cooled to 0° C. in an ice bath. 60 ml of 37% HCl is added, followed by a solution of NaNO2 (20.95 g, 0.307 mol) in 50 ml of H2O, through a dropping funnel, maintaining the temperature below 5° C. After the addition the mixture is left under stirring at between 0 and 5° C. for 1 h, and the solution obtained is added at 0° C. to a solution containing ethyl-2-chloroacetoacetate (41.65 g, 0.254 mol), AcONa (47.84 g, 0.583 mol), AcOEt (200 ml) and H2O (100 ml). The biphasic system is stirred at between 0 and 5° C. for 1 h, and then at about 25° C. for 16 h. The phases are then separated and the organic phase is washed with a saturated solution of NaHCO3 (4×80 ml), anhydrified on Na2SO4, filtered and evaporated under low pressure. The compound of formula (IV) is obtained as a solid (about 57 g), which is used for the next stage without further purification.

Aufarbeitung

  1. customequipped with coolant, thermometer,
  2. temperaturemaintaining the temperature below 5° C
  3. additionAfter the addition the mixture
  4. waitis left
  5. customthe solution obtained
  6. additionis added at 0° C. to a solution
  7. stirringThe biphasic system is stirred at between 0 and 5° C. for 1 h
  8. waitat about 25° C. for 16 h
  9. customThe phases are then separated
  10. washthe organic phase is washed with a saturated solution of NaHCO3 (4×80 ml)
  11. filtrationfiltered
  12. customevaporated under low pressure

Quellen und Nachweise

ORD-Eintrag
ord-61fbd5a9e2444c528befd0e0830cdb32
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969561B2

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