4-Nitrotoluene → N-(2-methyl-5-nitrobenzyl)benzamide

HRID 1075325

Reaktionsgleichung

Reaktionsgleichung von HRID 1075325
O[CH2:2][NH:3][C:4](=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)([O-:14])=[O:13]>S(=O)(=O)(O)O>[CH3:21][C:18]1[CH:19]=[CH:20][C:15]([N+:12]([O-:14])=[O:13])=[CH:16][C:17]=1[CH2:2][NH:3][C:4](=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Komponenten

4

Edukt 2

HCID 74734-NitrotolueneHCID 80493N-(hydroxymethyl)benzamide

Produkt 1

HCID 13115427N-(2-methyl-5-nitrobenzyl)benzamideAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

N-hydroxymethyl benzamide (7.55 g; 0.05 mol) is added to a solution of p-nitrotoluene (0.85 g; 0.05 mol) in concentrated sulfuric acid (60 ml). The reaction mixture is stirred for 63 hours at room temperature and then poured onto ice. A colorless precipitate is obtained which is isolated and recrystallized repeatedly from aqueous ethanol to give 4.0 g (i.e., 30% yield) of product. Increasing the reaction time to 7 days gives a 43% yield of product compound. This product has the following characteristics: melting point of 134° to 137° C.; i.r. 3300, 1635, 1655 cm-1 (sh); mass. spec. m/e 270.

Aufarbeitung

  1. additionpoured onto ice
  2. customA colorless precipitate is obtained which
  3. customis isolated
  4. customrecrystallized repeatedly from aqueous ethanol
  5. customto give 4.0 g (i.e., 30% yield) of product
  6. temperatureIncreasing the reaction time to 7 days

Quellen und Nachweise

ORD-Eintrag
ord-b52989311fb64ed1a0cd62a9b485a361
Quelldatensatz
uspto-grants-1983_07
Patentnummer
US04395577

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