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Furfurylamine → N-furfuryl-2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]butyramide

HRID 1995264
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1995264
[CH2:1]([NH2:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.[N+:8]([C:11]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][C:26]=2[Cl:35])=[CH:20][C:12]=1[O:13][CH:14]([CH2:18][CH3:19])[C:15](Cl)=[O:16])([O-:10])=[O:9]>C(Cl)Cl>[CH2:1]([NH:7][C:15](=[O:16])[CH:14]([O:13][C:12]1[CH:20]=[C:21]([O:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][C:26]=2[Cl:35])[CH:22]=[CH:23][C:11]=1[N+:8]([O-:10])=[O:9])[CH2:18][CH3:19])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 3438FurfurylamineHCID 204411292-[2-Nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]butyryl chloride

Produkt 1

HCID 20488082N-furfuryl-2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]butyramide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

Furfurylamine (0.015 mole) triethylamine (5 ml) and methylene chloride (50 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and addition funnel. The reaction mixture is cooled to about -15° C. and a solution of 2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]butyryl chloride (0.01 mole) in methylene chloride (50 ml) is added dropwise with stirring. After the addition is completed the reaction mixture is allowed to warm to room temperature with continued stirring. After this time the mixture is transferred to a separatory funnel and is washed with water and dilute aqueous sodium bicarbonate. The washed solution is then dried, filtered and stripped of solvent leaving a residue. This residue is then purified by subjecting it to elution chromatography using mixtures of ethyl acetate and hexane with increasing concentrations of ethyl acetate as the eluant. The desired fractions determined by IR spectroscopy are then stripped of solvent to yield the desired product N-furfuryl-2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]butyramide.

Aufarbeitung

  1. customequipped with a mechanical stirrer
  2. additionthermometer and addition funnel
  3. additionAfter the addition
  4. temperatureto warm to room temperature with continued stirring
  5. customAfter this time the mixture is transferred to a separatory funnel
  6. washis washed with water and dilute aqueous sodium bicarbonate
  7. customThe washed solution is then dried
  8. filtrationfiltered
  9. customleaving a residue
  10. customThis residue is then purified
  11. washto elution chromatography
  12. temperaturewith increasing concentrations of ethyl acetate as the eluant

Quellen und Nachweise

ORD-Eintrag
ord-69b68dbc462d4fa4adf38ef996df7e86
Quelldatensatz
uspto-grants-1983_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04404018

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