Diisobutylamine → HCID 21272460, Verbindung

HRID 1193538

Reaktionsgleichung

Reaktionsgleichung von HRID 1193538
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:5]=1[C:6]([OH:8])=O)([O-:3])=[O:2].[CH2:16]([NH:20][CH2:21][CH:22]([CH3:24])[CH3:23])[CH:17]([CH3:19])[CH3:18].P(Cl)(Cl)(Cl)=O.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[CH2:16]([N:20]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:6](=[O:8])[C:5]1[C:9]([N+:13]([O-:15])=[O:14])=[CH:10][CH:11]=[CH:12][C:4]=1[N+:1]([O-:3])=[O:2])[CH:17]([CH3:19])[CH3:18]

Komponenten

6

Edukt 4

HCID 8085DiisobutylamineHCID 24813Phosphorus oxychlorideHCID 119206Benzoic acid, 2,6-dinitro-HCID 516892Sodium Bicarbonate

Produkt 1

HCID 21272460HCID 21272460, VerbindungAusbeute 64,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a slurry of 106.5 g of 2,6-dinitrobenzoic acid in 1000 ml of toluene was added with stirring 133.2 g of diisobutylamine. Next 44.9 g of phosphorus oxychloride was added dropwise at such a rate to maintain the temperature below 40° C. The mixture was heated to 50° C. for 12 hrs and poured into 500 ml of aqueous 5% NaHCO3 solution with stirring. The organic layer was separated, washed with 500 ml water, and the toluene removed under reduced pressure. The remaining solid was recrystallized from hot ethanol to give 105.2 g of N,N-diisobutyl-2,6-dinitrobenzamide, a yellow solid, mp 97°-99° C.

Aufarbeitung

  1. temperatureto maintain the temperature below 40° C
  2. customThe organic layer was separated
  3. washwashed with 500 ml water
  4. customthe toluene removed under reduced pressure
  5. customThe remaining solid was recrystallized from hot ethanol

Quellen und Nachweise

ORD-Eintrag
ord-2c7d3a4bb767437e821819555240276b
Quelldatensatz
uspto-grants-1989_03
Patentnummer
US04810769

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