Pyridine → N-(2,4-Dimethylphenyl)-2-(2-fluoroacetamido)-5-nitrobenzamide

HRID 986647Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 986647
[NH2:1][C:2]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:8]=1[CH3:14])=[O:5].N1C=CC=CC=1.[F:28][CH2:29][C:30](Cl)=[O:31]>O1CCCC1>[F:28][CH2:29][C:30]([NH:1][C:2]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:8]=1[CH3:14])=[O:5])=[O:31]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 9663Fluoroacetyl chlorideHCID 133764472-Amino-N-(2,4-dimethylphenyl)-5-nitrobenzamide

Produkt 1

HCID 13376455N-(2,4-Dimethylphenyl)-2-(2-fluoroacetamido)-5-nitrobenzamideAusbeute 88,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4.0 g of N-(2-amino-5-nitrobenzoyl)-2,4-dimethylaniline and 2.36 g of pyridine are dissolved in 50 ml of tetrahydrofuran, and 2.18 g of fluoracetyl chloride are added dropwise thereto under ice-cooling. The mixture is then stirred at room temperature for 5 hours. The mixture is concentrated under reduced pressure to remove tetrahydrofuran, and 100 ml of water are added to the residue. Crystalline precipitates are collected by filtration and recrystallized from a mixture of dimethylformamide and ethanol (1:2). 4.3 g of N-(2-fluoroacetamido-5-nitrobenzoyl)-2,4-dimethylaniline are obtained as colorless needles.

Aufarbeitung

  1. temperatureunder ice-cooling
  2. concentrationThe mixture is concentrated under reduced pressure
  3. customto remove tetrahydrofuran, and 100 ml of water
  4. additionare added to the residue
  5. customCrystalline precipitates
  6. filtrationare collected by filtration
  7. customrecrystallized from a mixture of dimethylformamide and ethanol (1:2)

Quellen und Nachweise

ORD-Eintrag
ord-7e762bc7c49c443ab6791667982ca6d3
Quelldatensatz
uspto-grants-1987_12
Patentnummer
US04714702

Notizen zur Reaktion

Wird geladen…