Sulfuric Acid → Methyl 4-amino-5-fluoro-3-chloro-6-(4-chlorophenyl)picolinate

HRID 1774284Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1774284
COC1C=CC([NH:9][C:10]2[C:15]([F:16])=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[N:13]=[C:12]([C:24]([O:26][CH3:27])=[O:25])[CH:11]=2)=CC=1.[Cl:28]N1C(C)(C)C(=O)N(Cl)C1=O.S(=O)(=O)(O)O.C(Cl)Cl>C(#N)C.O>[NH2:9][C:10]1[C:15]([F:16])=[C:14]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:13]=[C:12]([C:24]([O:26][CH3:27])=[O:25])[C:11]=1[Cl:28]

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 86723349Methyl 4-(4-methoxyphenylamino)-5-fluoro-6-(4-chlorophenyl)picolinate

Produkt 1

HCID 22677303Methyl 4-amino-5-fluoro-3-chloro-6-(4-chlorophenyl)picolinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18373917Acetonitrile--water (1/1)Lösungsmittel

Versuchsvorschrift

In a typical reaction accomplishing both chlorination and deprotection, methyl 4-(4-methoxyphenylamino)-5-fluoro-6-(4-chlorophenyl)picolinate is reacted with about two equivalents of 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione in the presence of a 1 M (molar) solution of sulfuric acid in a mixture of acetonitrile/water. The mixture is heated at reflux until the reaction is complete. The mixture is added to methylene chloride and the organic layer is separated, washed with brine and dried. The solvent is evaporated to provide crude methyl 4-amino-5-fluoro-3-chloro-6-(4-chlorophenyl)picolinate.

Aufarbeitung

  1. customIn a typical reaction
  2. temperatureThe mixture is heated
  3. temperatureat reflux until the reaction
  4. customthe organic layer is separated
  5. washwashed with brine
  6. customdried
  7. customThe solvent is evaporated

Quellen und Nachweise

ORD-Eintrag
ord-e9c59ea5d0594784b7fa0121174f2fcd
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09260392B2

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