4-Chloro-5-fluoro-1,2-phenylenediamine → 5-chloro-6-fluoro-2-methyl-1H-benzimidazole

HRID 658093

Reaktionsgleichung

Reaktionsgleichung von HRID 658093
[C:1]([O-])([O-])(OCC)[CH3:2].[Cl:8][C:9]1[CH:10]=[C:11]([NH2:17])[C:12]([NH2:16])=[CH:13][C:14]=1[F:15]>C(O)C>[Cl:8][C:9]1[C:14]([F:15])=[CH:13][C:12]2[NH:16][C:1]([CH3:2])=[N:17][C:11]=2[CH:10]=1

Komponenten

4

Edukt 2

HCID 7357734-Chloro-5-fluoro-1,2-phenylenediamineHCID 86598186Ethyl ortho-acetate

Produkt 1

HCID 552815655-chloro-6-fluoro-2-methyl-1H-benzimidazoleAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

A 4.96 g portion of ethyl orthoacetate dissolved in 10 ml of ethanol was added to 50 ml of ethanol solution containing 4.68 g of 4-chloro-5-fluorobenzene-1,2-diamine and heated under reflux for 4 hours. After concentration of the reaction liquid, the thus formed residue was purified by a silica gel column chromatography to obtain 2.10 g (39%) of 5-chloro-6-fluoro-2-methyl-1H-benzimidazole from a chloroform-methanol (10:1) eluate. ES+: 185

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. customAfter concentration of the reaction liquid
  4. customthe thus formed residue was purified by a silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3808743c057d473893bf85eb35750524
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076367B2

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