Phthaloyl chloride → 2-Fluoromethyl-2-phthalimido-5-methoxypentanenitrile

HRID 1252564

Reaktionsgleichung

Reaktionsgleichung von HRID 1252564
[F:1][CH2:2][C:3]([NH2:11])([CH2:6][CH2:7][CH2:8][O:9][CH3:10])[C:4]#[N:5].C(N(CC)CC)C.[C:19](Cl)(=[O:29])[C:20]1[C:21](=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:22](Cl)=[O:23]>C(Cl)Cl>[F:1][CH2:2][C:3]([N:11]1[C:22](=[O:23])[C:21]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]2[C:19]1=[O:29])([CH2:6][CH2:7][CH2:8][O:9][CH3:10])[C:4]#[N:5]

Komponenten

5

Edukt 3

HCID 6955Phthaloyl chlorideHCID 8471TriethylamineHCID 199663342-Amino-2-(fluoromethyl)-5-methoxypentanenitrile

Produkt 1

HCID 199663292-Fluoromethyl-2-phthalimido-5-methoxypentanenitrileAusbeute 82,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 2-fluoromethyl-2-amino-5-methoxypentanenitrile (1.62 g, 10 mmol) and triethylamine (2.02 g, 20 mmol) in methylene chloride (30 ml), cooled to -20° C., is added phthaloyldichloride (2.03 g, 10 mmol) in methylene chloride (10 ml). The mixture is allowed to warm up to room temperature overnight. After washing with water, 1N HCl, water again, and drying (Na2SO4), the solvent is removed under reduced pressure to give 2.4 g of crude material. This is purified by chromatography on silica (ethyl acetate/petroleum ether 3:7).

Aufarbeitung

  1. washAfter washing with water, 1N HCl, water again
  2. dry with materialdrying (Na2SO4)
  3. customthe solvent is removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f102d11c384048eeaac8cb3e971c5ea6
Quelldatensatz
uspto-grants-1988_05
Patentnummer
US04743691

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