Sodium Iodide → alpha-(5-Iodopentyl)-3,4-dimethoxy-alpha-[(4-methylphenyl)thio]benzeneacetonitrile

HRID 863874Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 863874
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([S:20][C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1)[C:8]#[N:9].[I-:28].[Na+]>CC(C)=O>[I:28][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([S:20][C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1)[C:8]#[N:9]

Komponenten

4

Edukt 2

HCID 5238Sodium IodideHCID 10573255alpha-(5-Chloropentyl)-3,4-dimethoxy-alpha-[(4-methylphenyl)-thio]benzeneacetonitrile

Produkt 1

HCID 19042083alpha-(5-Iodopentyl)-3,4-dimethoxy-alpha-[(4-methylphenyl)thio]benzeneacetonitrileAusbeute 96,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 0.86 g of α-(5-chloropentyl)-3,4-dimethoxy-α-[(4-methylphenyl)thio]benzeneacetonitrile, 3.2 g of sodium iodide, and 10 mL of acetone is heated to reflux overnight, protected from light. The volatiles are removed in vacuo and 30 mL of diethyl ether is added to the residue. The insolubles are collected and the volatiles removed in vacuo. The residue is purified via column chromatography using hexane/ethyl acetate (2:1) to afford 1.02 g of the desired product as a clear oil. MS(CI): m/z 496(M+H).

Aufarbeitung

  1. temperatureis heated
  2. temperatureto reflux overnight
  3. customThe volatiles are removed in vacuo and 30 mL of diethyl ether
  4. additionis added to the residue
  5. customThe insolubles are collected
  6. customthe volatiles removed in vacuo
  7. customThe residue is purified via column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c40f8e911be443e2813ac3413ba28f76
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05561141

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