STK017412 → HCID 13014260, Verbindung

HRID 1905830Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1905830
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][CH2:10][C:11]([NH:13][NH2:14])=[O:12].Cl.[C:16](=N)(OCC)[CH3:17]>N1C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][CH2:10][C:11]1[O:12][C:16]([CH3:17])=[N:14][N:13]=1

Komponenten

4

Edukt 2

HCID 302666STK017412HCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)

Produkt 1

HCID 13014260HCID 13014260, VerbindungAusbeute 34,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A solution of 19.3 g (0.1 mol) alpha-(2,6-dimethylphenylamino)acethydrazide and 14 g (0.11 mol) ethyl actimidate hydrochloride (Aldrich Chemical Co.) in 150 ml pyridine was heated under reflux for 9 hours. The reaction mixture was filtered and the filtrate was evaporated under reduced pressure to give an oil. The oil was placed on 400 g silica gel in a chromatography column and eluted the following solvent systems: (1) petroleum ether, (2) petroleum ether/ethyl ether, (3) ethyl ether, and (4) ethyl ether/methanol. The crude product (11.5 g) was eluted from the column with the ethyl ether/methanol solvent system. Crystallization of the crude product from dichloromethane/ethyl ether gave 7.4 g of crystalline product, m.p. 134°-135° C. The product is tabulated in Table I as Compound No. 1-A.

Aufarbeitung

  1. temperatureunder reflux for 9 hours
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated under reduced pressure
  4. customto give an oil
  5. washeluted the following solvent systems
  6. washThe crude product (11.5 g) was eluted from the column with the ethyl ether/methanol solvent system
  7. customCrystallization of the crude product from dichloromethane/ethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-446930e9530e4d54be7a01d63b6bfe3e
Quelldatensatz
uspto-grants-1987_03
Patentnummer
US04648897

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