Dimethylformamide → Methyl 2-(cyclohexen-3-yloxy)-4-acetylamino-5-chlorobenzoate

HRID 5880

Reaktionsgleichung

Reaktionsgleichung von HRID 5880
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([OH:16])[C:8](=[CH:13][C:14]=1[Cl:15])[C:9]([O:11][CH3:12])=[O:10])(=[O:3])[CH3:2].Br[CH:18]1[CH2:23][CH2:22][CH2:21][CH:20]=[CH:19]1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>O>[CH:18]1[CH2:23][CH2:22][CH2:21][CH:20]([O:16][C:7]2[CH:6]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[C:14]([Cl:15])=[CH:13][C:8]=2[C:9]([O:11][CH3:12])=[O:10])[CH:19]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 1370573-BromocyclohexeneHCID 13329485Methyl 4-acetamido-5-chloro-2-hydroxybenzoate

Produkt 1

HCID 14621154Methyl 2-(cyclohexen-3-yloxy)-4-acetylamino-5-chlorobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 2.5 g methyl 4-acetylamino-5chlorosalicylate, 2 g of 3-bromocyclohexene, 2 g K2CO3 and 30 ml DMF are combined and heated at 110° C. overnight. The reaction mixture is then poured into water, filtered, dried and then extracted into ether. The ether solution is treated with charcoal, filtered and evaporated to dryness to obtain methyl 2-(cyclohexen -3-yloxy)-4-acetylamino-5-chlorobenzoate. This is then purified by recrystallization from ether/hexane. (M.P. 100°-102° C.)

Aufarbeitung

  1. filtrationfiltered
  2. customdried
  3. extractionextracted into ether
  4. additionThe ether solution is treated with charcoal
  5. filtrationfiltered
  6. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-a899c80f18084f9c9768df737127ddcc
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246942

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