4-Methyl-3-nitroaniline → N-(4-Methyl-3-nitrophenyl)-3-(trifluoromethyl)benzamide

HRID 967890

Reaktionsgleichung

Reaktionsgleichung von HRID 967890
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].[N+:14]([C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][C:23]=1[CH3:24])[NH2:20])([O-:16])=[O:15]>N1C=CC=CC=1>[CH3:24][C:23]1[CH:22]=[CH:21][C:19]([NH:20][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][CH:11]=[C:3]([C:2]([F:13])([F:12])[F:1])[CH:4]=2)=[CH:18][C:17]=1[N+:14]([O-:16])=[O:15]

Komponenten

4

Edukt 2

HCID 83904-Methyl-3-nitroanilineHCID 752573-(Trifluoromethyl)benzoyl chloride

Produkt 1

HCID 11716802N-(4-Methyl-3-nitrophenyl)-3-(trifluoromethyl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 3-trifluoromethylbenzoyl chloride (9.9 ml), 3-nitro-4-methylaniline (10 g) and pyridine (100 ml) was stirred and heated to 80° C. for 2 hours. The reaction mixture was evaporated and the residue was triturated under 2N aqueous hydrochloric acid solution. The solid so obtained was isolated, washed in turn with a saturated aqueous sodium bicarbonate solution, water and isohexane and dried under vacuum at 55° C. to give N-(4-methyl-3-nitrophenyl)-3-trifluoromethylbenzamide as a solid (21.9 g); NMR Spectrum: (DMSOd6) 7.49 (d, 1H), 7.78 (m, 1H), 7.99 (m, 2H), 8.27 (m, 2H), 8.51 (s, 1H), 10.77 (s, 1H); Mass Spectrum: M−H− 23.

Aufarbeitung

  1. customThe reaction mixture was evaporated
  2. customthe residue was triturated under 2N aqueous hydrochloric acid solution
  3. customThe solid so obtained
  4. customwas isolated
  5. washwashed in turn with a saturated aqueous sodium bicarbonate solution, water and isohexane
  6. customdried under vacuum at 55° C.

Quellen und Nachweise

ORD-Eintrag
ord-ebeb4a8f63ed4958bd3863cb65cadbbb
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06956037B2

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