Dimethylformamide → 1-Amino-1-(4-methoxycarbonylphenyl)-3-oxo-3-(4-pentyloxyphenyl)-1-propene

HRID 1816780Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1816780
C[N:2](C)C=O.[CH3:6][O:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16](=O)[CH2:17][C:18]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:22][CH:21]=2)=[O:19])=[CH:12][CH:11]=1)=[O:9].C([O-])=O.[NH4+].C(OCC)(=O)C>O>[NH2:2][C:16]([C:13]1[CH:14]=[CH:15][C:10]([C:8]([O:7][CH3:6])=[O:9])=[CH:11][CH:12]=1)=[CH:17][C:18](=[O:19])[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:22][CH:21]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 2723923Ammonium formateHCID 11405985Methyl 4-[1,3-dioxo-3-[4-(pentyloxy)phenyl]propyl]benzoate

Produkt 1

HCID 696777131-Amino-1-(4-methoxycarbonylphenyl)-3-oxo-3-(4-pentyloxyphenyl)-1-propene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Dimethylformamide (123 l), 1-(4-methoxycarbonylphenyl)-3-(4-pentyloxyphenyl)propane-1,3-dione (24.5 kg) and ammonium formate (21.0 kg) were charged in 2000-liter reactor at room temperature and heated, and a reaction was carried out at the inner temperature of 100 to 105° C. for 5 hours. After completion of the reaction, the mixture was cooled down to room temperature, ethyl acetate (613 l) and water (613 l) were added, the mixture was stirred, and an ethyl acetate layer was separated, and then washed with 10% sodium chloride solution (613 l) and with 20% sodium chloride solution (613 l). The ethyl acetate layer was concentrated in vacuo to 125 l and then diluted with n-heptane (625 l) at the inner temperature of 40 to 45° C. to separate crystals of 1-amino-1-(4-methoxycarbonylphenyl)-3-oxo-3-(4-pentyloxyphenyl)-1-propene. The cyrstals were filtered at room temperature and washed with a mixture of n-heptane (104 l) and ethyl acetate (21 l). The crystals were dried overnight in vacuo and purified by suspending in a 70% aqueous acetone (158 l) to give 1-amino-1-(4-methoxycarbonylphenyl)-3-oxo-3-(4-pentyloxyphenyl)-1-propene (14.3 kg).

Aufarbeitung

  1. temperatureheated
  2. customAfter completion of the reaction
  3. customan ethyl acetate layer was separated
  4. washwashed with 10% sodium chloride solution (613 l) and with 20% sodium chloride solution (613 l)
  5. concentrationThe ethyl acetate layer was concentrated in vacuo to 125 l
  6. additiondiluted with n-heptane (625 l) at the inner temperature of 40 to 45° C.
  7. customto separate crystals of 1-amino-1-(4-methoxycarbonylphenyl)-3-oxo-3-(4-pentyloxyphenyl)-1-propene
  8. filtrationThe cyrstals were filtered at room temperature
  9. washwashed with a mixture of n-heptane (104 l) and ethyl acetate (21 l)
  10. customThe crystals were dried overnight in vacuo
  11. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-e22f239b382741cb96a3c01dfd9faa4a
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06884868B1

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