Hydrochloric Acid → HCID 178496277, Verbindung

HRID 1624584Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1624584
[N:1]([O-])=O.[Na+].[F:5][C:6]([F:15])([F:14])[C:7]1[CH:8]=[C:9]([CH:11]=[CH:12][CH:13]=1)[NH2:10].Cl.[CH3:17][O:18][CH2:19][C:20](=[O:26])[CH2:21][C:22]([O:24][CH3:25])=[O:23].CC([O-])=O.[Na+]>O.CCO>[CH3:17][O:18][CH2:19][C:20](=[O:26])[C:21](=[N:1][NH:10][C:9]1[CH:11]=[CH:12][CH:13]=[C:7]([C:6]([F:14])([F:15])[F:5])[CH:8]=1)[C:22]([O:24][CH3:25])=[O:23]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 73753-(Trifluoromethyl)anilineHCID 123500Methyl 4-methoxyacetoacetateHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Produkt 1

HCID 178496277HCID 178496277, VerbindungAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of NaNO2 (4.14 g, 60 mmol) in H2O (15 mL) was added dropwise at 0° C. to a mixture of 3-(trifluoromethyl)aniline (6.24 mL, 50 mmol) and 6 M HCl aqueous solution (50 mL, 300 mmol). After stirring for 15 min, the resulting aqueous solution was added to a suspension of methyl 4-methoxyacetoacetate (7.31 mL, 50 mmol) and NaOAc (24.6 g, 300 mmol) in EtOH (80 mL) pre-cooled at 0° C. The precipitate was collected by filtration, washed with water, and dissolved in AcOEt. The organic solution was washed with water and brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was crystallized from hexane/AcOEt to give the title compound (14.0 g, 88% yield) as pale yellow crystals: 1H NMR (300 MHz, CDCl3): δ ppm 3.51 (3H×0.36, s), 3.52 (3H×0.64, s), 3.90 (3H×0.36, s), 3.94 (3H×0.64, s), 4.68 (2H×0.64, s), 4.70 (2H×0.36, s), 7.41-7.59 (3H+1H×0.64, m), 7.71 (1H×0.36, s), 13.00 (1H×0.64, s), 14.87 (1H×0.36, s).

Aufarbeitung

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water
  3. dissolutiondissolved in AcOEt
  4. washThe organic solution was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was crystallized from hexane/AcOEt

Quellen und Nachweise

ORD-Eintrag
ord-606fdc5ac1b84ff8ba0d2cfc2a5ab836
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778944B2

Notizen zur Reaktion

Wird geladen…