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4-Nitroaniline → HCID 69202260, Verbindung

HRID 1394117
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1394117
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=1)=O)[CH3:2].[N+:16]([C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1)([O-:18])=[O:17].Cl.[N+]([C:30]1C=CC(N)=C[CH:31]=1)([O-])=O>C(O)CCC>[CH2:1]([O:3][C:4](=[O:15])[CH:5]=[C:6]([NH:23][C:22]1[CH:24]=[CH:25][C:19]([N+:16]([O-:18])=[O:17])=[CH:20][CH:21]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=1)[CH2:2][CH2:30][CH3:31]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 74754-NitroanilineHCID 851564-Nitroanilinium chlorideHCID 2063904Ethyl 3-(3-fluorophenyl)-3-oxopropanoate

Produkt 1

HCID 69202260HCID 69202260, VerbindungAusbeute 434,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
118 °C

Versuchsvorschrift

Into a dry 2 L round-bottom flask was placed 106.3 grams (0.506 moles) of 3-(3-fluorophenyl)-3-oxo-propionic acid ethyl ester, 63.0 grams (0.456 moles) of 4-nitro-aniline and 4.0 grams (0.023 moles) of 4-nitro-aniline hydrochloride. To the mixture was added 1.3 L of n-butanol, the flask was fitted with a Soxhlet extractor (cup volume of 0.3 L), condenser and nitrogen inlet. Dry, activated 4 Å sieves (200 grams) were placed in the extractor cup and the reaction mixture heated to reflux temperature of 118° C. under nitrogen and maintained at that temperature for 90 hours. The reaction mixture was decanted while hot from a small amount of solids and chilled to −15° C. for 48 hours Crystalline solids were collected by vacuum filtration. The crystals were washed with 0.2 L of cold ethanol and two 0.2 L portions of hexanes and vacuum dried at 50° C. overnight to yield 35.8 grams (20.8% yield) of the title compound.

Aufarbeitung

  1. customInto a dry 2 L round-bottom flask was placed
  2. customthe flask was fitted with a Soxhlet extractor (cup volume of 0.3 L), condenser and nitrogen inlet
  3. customDry
  4. temperaturethe reaction mixture heated
  5. temperaturemaintained at that temperature for 90 hours
  6. customThe reaction mixture was decanted while hot from a small amount of solids
  7. temperaturechilled to −15° C. for 48 hours Crystalline solids
  8. filtrationwere collected by vacuum filtration
  9. washThe crystals were washed with 0.2 L of cold ethanol and two 0.2 L portions of hexanes and vacuum
  10. customdried at 50° C. overnight

Quellen und Nachweise

ORD-Eintrag
ord-64036b15394d4b4da4463e012608b63a
Quelldatensatz
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07348340B2

Notizen zur Reaktion

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