2,5-Dichlorobenzoic acid → 5-Chloro-2-[2-methyl-3-(trifluoromethyl)anilino]benzoic acid

HRID 437198

Reaktionsgleichung

Reaktionsgleichung von HRID 437198
Cl[C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(O)CCCC.[OH-].[Na+].[CH3:20][C:21]1[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:25]=[CH:24][C:22]=1[NH2:23]>[Cu]>[Cl:11][C:8]1[CH:7]=[C:3]([C:4]([OH:6])=[O:5])[C:2]([NH:23][C:22]2[CH:24]=[CH:25][CH:26]=[C:27]([C:28]([F:29])([F:30])[F:31])[C:21]=2[CH3:20])=[CH:10][CH:9]=1

Komponenten

6

Edukt 4

HCID 57842,5-Dichlorobenzoic acidHCID 62761-PentanolHCID 14798Sodium HydroxideHCID 2735932Trifluoromethyl toluidine

Produkt 1

HCID 451177035-Chloro-2-[2-methyl-3-(trifluoromethyl)anilino]benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23978CopperKatalysator

Versuchsvorschrift

To a solution of 25 g. of 2,5-dichlorobenzoic acid in 125 ml. of n-pentyl alcohol add 4.8 g. of sodium hydroxide pellets, 25 g. of 2-methyl-3-trifluoromethylaniline and 2 g. of copper powder. With constant stirring, reflux the reaction mixture for 18 hours. Concentrate the mixture to one half volume and dilute with water and ether. Acidify the aqueous layer to yield the product which is recrystallized from methanol, m.p. 220°-222° C.

Aufarbeitung

  1. temperatureWith constant stirring, reflux the reaction mixture for 18 hours
  2. concentrationConcentrate the mixture to one half volume
  3. additiondilute with water and ether
  4. customto yield the product which
  5. customis recrystallized from methanol, m.p. 220°-222° C.

Quellen und Nachweise

ORD-Eintrag
ord-4d4f4c4afad6436984261a6ffd258e11
Quelldatensatz
uspto-grants-1977_06
Patentnummer
US04029815

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