HCID 20441164, Verbindung → HCID 20441130, Verbindung

HRID 1632909Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1632909
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[CH2:7][NH2:8].[N+:9]([C:12]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[C:32]#[N:33])=[CH:20][C:13]=1[O:14][CH:15]([CH3:19])[C:16](Cl)=[O:17])([O-:11])=[O:10]>C(Cl)Cl>[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[CH2:7][NH:8][C:16](=[O:17])[CH:15]([O:14][C:13]1[CH:20]=[C:21]([O:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[C:32]#[N:33])[CH:22]=[CH:23][C:12]=1[N+:9]([O-:11])=[O:10])[CH3:19]

Komponenten

4

Edukt 2

HCID 20441164HCID 20441164, VerbindungHCID 212488031-(1,3-Dioxan-2-yl)methanamine

Produkt 1

HCID 20441130HCID 20441130, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

N-(1,3-Dioxan-2-ylmethyl)amine (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-cyano-4-fluorophenoxy)phenoxy]propionyl 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. The residue is then recrystallized from a toluene/hexane mixture to yield the desired product N-(1,3-dioxan-2-ylmethyl)-2-[2-nitro-5-(2-cyano-4-fluorophenoxy)phenoxy]propionamide.

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. customThe residue is then recrystallized from a toluene/hexane mixture

Quellen und Nachweise

ORD-Eintrag
ord-000c56d7b5b04a1f8f921fb5630859e8
Quelldatensatz
uspto-grants-1984_10
Patentnummer
US04478634

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