Propionic Acid → Flumiclorac-pentyl

HRID 704092

Reaktionsgleichung

Reaktionsgleichung von HRID 704092
[Cl:1][C:2]1[C:8]([O:9][CH2:10][C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:12])=[CH:7][C:5]([NH2:6])=[C:4]([F:19])[CH:3]=1.[C:20]1(=O)[O:25][C:23](=[O:24])[C:22]2[CH2:26][CH2:27][CH2:28][CH2:29][C:21]1=2.C(O)(=O)CC.C1(C)C=CC=CC=1>N1CCCCC1.O>[Cl:1][C:2]1[C:8]([O:9][CH2:10][C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:12])=[CH:7][C:5]([N:6]2[C:23](=[O:24])[C:22]3[CH2:26][CH2:27][CH2:28][CH2:29][C:21]=3[C:20]2=[O:25])=[C:4]([F:19])[CH:3]=1

Komponenten

7

Edukt 4

HCID 1032Propionic AcidHCID 1140TolueneHCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 146178504-Chloro-2-fluoro-5-(pentyloxycarbonylmethyloxy)aniline

Produkt 1

HCID 443048Flumiclorac-pentylAusbeute 91,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8082PiperidineKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of the compound (II) (12.0 g), 3,4,5,6-tetrahydrophthalic anhydride (7.56 g), piperidine (0.18 g), propionic acid (0.30 g) and toluene (24 g) was heated under reflux for 5 hours, during which water as by-produced was azeotropically removed. To the reaction mixture, toluene (24 g) and water (24 g) were added, and the organic layer was separated and concentrated under reduced pressure. To the residue, water (18 g) and methanol (33 g) were added, and the precipitated crystals were collected by filtration to give N-[4-chloro-2-fluoro-5-(pentyloxycarbonylmethyloxy)-phenyl]-3,4,5,6-tetrahydrophthalimide (Compound (I)) (16.1 g). By the use of a high speed liquid chromatography, the purity of the compound (I) as the major product and the amount of the by-produced 4-chloro-2-fluoro-5-(pentyloxycarbonylmethyloxy)acetanilide (hereinafter referred to as "N-acetyl compound") as a contaminant were determined according to the inner standard method and the area comparison method, respectively.

Aufarbeitung

  1. temperaturewas heated
  2. customas by-produced
  3. customwas azeotropically removed
  4. additionTo the reaction mixture, toluene (24 g) and water (24 g) were added
  5. customthe organic layer was separated
  6. concentrationconcentrated under reduced pressure
  7. additionTo the residue, water (18 g) and methanol (33 g) were added
  8. filtrationthe precipitated crystals were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-3e7e70920c744ff6a71054931254e25f
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04985570

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