Hexanoyl chloride → 4-Hexanamidophthalonitrile

HRID 650688

Reaktionsgleichung

Reaktionsgleichung von HRID 650688
[NH2:1][C:2]1[CH:3]=[C:4]([C:10]#[N:11])[C:5](=[CH:8][CH:9]=1)[C:6]#[N:7].[C:12](Cl)(=[O:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>N1C=CC=CC=1.ClCCl>[C:12]([NH:1][C:2]1[CH:3]=[C:4]([C:10]#[N:11])[C:5](=[CH:8][CH:9]=1)[C:6]#[N:7])(=[O:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Komponenten

5

Edukt 2

HCID 67340Hexanoyl chlorideHCID 925291,2-Benzenedicarbonitrile, 4-amino-

Produkt 1

HCID 184663724-HexanamidophthalonitrileAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-Aminophthalonitrile (3.60 g, 25.2 2.mmole) was dissolved in 8.6 mL of pyridine. Hexanoyl chloride (8.6 10, 61.5 mmole) was added and the mixture was stirred under N2 for 2 hours. The pyridine was distilled under vacuum until a yellow-orange residue was obtained. This residue was dissolved in dichloromethane and washed with 0.1 M HCl (5×15 mL) and then neutralized with aqueous sodium bicarbonate (3×50 mL). The organic solution was separated and dried over magnesium sulfate. Purification by column chromatography (silica, dichloromethane: methanol 5%) afforded 4.3 g (71% yield) of 4-hexanamidophthalonitrile as a light yellow compound.

Aufarbeitung

  1. distillationThe pyridine was distilled under vacuum until a yellow-orange residue
  2. customwas obtained
  3. washwashed with 0.1 M HCl (5×15 mL)
  4. customThe organic solution was separated
  5. dry with materialdried over magnesium sulfate
  6. customPurification by column chromatography (silica, dichloromethane: methanol 5%)

Quellen und Nachweise

ORD-Eintrag
ord-e3b80cb6e1b840558b6345b543a20676
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06274729B1

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