2,6-Dimethylaniline → N-(2,6-Dimethylphenyl)-4-nitrobenzamide

HRID 973709

Reaktionsgleichung

Reaktionsgleichung von HRID 973709
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].C(=O)([O-])[O-].[K+].[K+].[N+:16]([C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1)([O-:18])=[O:17]>O1CCCC1>[N+:16]([C:19]1[CH:20]=[CH:21][C:22]([C:23]([NH:4][C:3]2[C:5]([CH3:9])=[CH:6][CH:7]=[CH:8][C:2]=2[CH3:1])=[O:24])=[CH:26][CH:27]=1)([O-:18])=[O:17]

Komponenten

5

Edukt 3

HCID 68962,6-DimethylanilineHCID 85024-Nitrobenzoyl chlorideHCID 11430Potassium Carbonate

Produkt 1

HCID 477704N-(2,6-Dimethylphenyl)-4-nitrobenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 0.09 moles of 2,6-dimethyl-aniline in 35 ml of tetrahydrofuran was added to 200 ml of 20% (w/v) aqueous potassium carbonate contained in a one liter flask. A solution of 20 g of p-nitrobenzoyl chloride in 35 ml of tetrahydrofuran was added dropwise. The resulting mixture was refluxed for 12 hours while the pH was maintained at or above pH 8. The solution was cooled to room temperature and extracted three times, each with 100 ml of chloroform. The extracts were combined, dried over magnesium sulfate, and evaporated in vacuo. The resulting residue was crystallized from petroleum ether/benzene affording 15 g of the desired subtitle intermediate, m.p. 192-194.

Aufarbeitung

  1. customcontained in a one liter flask
  2. temperatureThe resulting mixture was refluxed for 12 hours while the pH
  3. temperaturewas maintained at or above pH 8
  4. extractionextracted three times
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe resulting residue was crystallized from petroleum ether/benzene affording 15 g of the desired subtitle intermediate, m.p. 192-194

Quellen und Nachweise

ORD-Eintrag
ord-a1d3ec810ca944548d66c9da4648afa1
Quelldatensatz
uspto-grants-1991_11
Patentnummer
US05064862

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