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Dimethylformamide → N,N'-didecyl-5-nitro-1,3-benzenedicarboxamide

HRID 1757779
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1757779
[N+:1]([C:4]1[CH:5]=[C:6]([C:13]([OH:15])=O)[CH:7]=[C:8]([CH:12]=1)[C:9]([OH:11])=O)([O-:3])=[O:2].C[N:17]([CH:19]=O)C.[CH2:21]([NH2:31])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C(N([CH2:37][CH3:38])CC)C>S(Cl)(Cl)=O.O1CCCC1.O>[CH2:21]([NH:31][C:9]([C:8]1[CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[C:6]([C:13]([NH:17][CH2:19][CH2:7][CH2:6][CH2:5][CH2:4][CH2:12][CH2:8][CH2:9][CH2:37][CH3:38])=[O:15])[CH:7]=1)=[O:11])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 8916DecylamineHCID 120695-Nitroisophthalic acid

Produkt 1

HCID 19388993N,N'-didecyl-5-nitro-1,3-benzenedicarboxamideAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962
Water
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel
HCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

To 30 g (0.14 mol) of 5-nitroisophthalic acid suspended in 120 ml of thionyl chloride was added 2 ml of DMF and the solution was stirred at reflux for 3.5 hours. The excess thionyl chloride was removed at reduced pressure and the residual acid chloride was dissolved in 220 ml of anhydrous tetrahydrofuran. This solution was added dropwise to 64 ml (0.32mol) of decyl amine and 44 ml (0.32 mol) of triethylamine in 350 ml of anhydrous tetrahydrofuran over 30 minutes with ice bath cooling. The reaction mixture was stirred at room temperature for 4 hours and then poured into 3 L of water. The resultant solid was removed by filtration and recrystallized from methanol to give 51.5 g (74% yield, mp 115°-116°) of N,N'-didecyl-5-nitro-1,3-benzenedicarboxamide.

Aufarbeitung

  1. temperatureat reflux for 3.5 hours
  2. customThe excess thionyl chloride was removed at reduced pressure
  3. dissolutionthe residual acid chloride was dissolved in 220 ml of anhydrous tetrahydrofuran
  4. temperaturecooling
  5. stirringThe reaction mixture was stirred at room temperature for 4 hours
  6. customThe resultant solid was removed by filtration
  7. customrecrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-58e8780dd70c4d5295fb23e3bbdb6667
Quelldatensatz
uspto-grants-1995_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05446189

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