Sodium Cyanide → 3-Cyanomethyl-5-(3-fluoro-4-phenyl-alpha-methylbenzyl)-1,2,4-oxadiazole

HRID 2290770Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2290770
Cl[CH2:2][C:3]1[N:7]=[C:6]([CH:8]([CH3:22])[C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11]([F:21])[CH:10]=2)[O:5][N:4]=1.[C-:23]#[N:24].[Na+]>CS(C)=O>[C:23]([CH2:2][C:3]1[N:7]=[C:6]([CH:8]([CH3:22])[C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11]([F:21])[CH:10]=2)[O:5][N:4]=1)#[N:24]

Komponenten

4

Edukt 2

HCID 8929Sodium CyanideHCID 136909413-Chloromethyl-5-(3-fluoro-4-phenyl-alpha-methylbenzyl)-1,2,4-oxadiazole

Produkt 1

HCID 136909683-Cyanomethyl-5-(3-fluoro-4-phenyl-alpha-methylbenzyl)-1,2,4-oxadiazoleAusbeute 64,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a solution of 3.82 g of 3-chloromethyl-5-(3-fluoro-4-phenyl-α-methylbenzyl)-1,2,4-oxadiazole in 50 ml of dimethyl sulfoxide (DMSO) was added 0.75 g of sodium cyanide. After stirring for 1 hour at room temperature, the reaction mixture was poured into ice-water. The resultant mixture was extracted with benzene and the extracts were washed with water, dried over sodium sulfate and evaporated. The residue was chromatographed over silica gel using benzene to yield 2.4 g of 3-cyanomethyl-5-(3-fluoro-4-phenyl-α-methylbenzyl)-1,2,4-oxadiazole. It was recrystallized from ethyl acetate-diisopropyl ether to give colorless plates, m.p. 111°-112° C.

Aufarbeitung

  1. extractionThe resultant mixture was extracted with benzene
  2. washthe extracts were washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue was chromatographed over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-f9d40fd4cee945d3b940facc7be6ee49
Quelldatensatz
uspto-grants-1986_10
Patentnummer
US04618617

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