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

HRID 863874Notes

Reaction equation

HRID 863874 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

HCID 19042083alpha-(5-Iodopentyl)-3,4-dimethoxy-alpha-[(4-methylphenyl)thio]benzeneacetonitrileYield 96.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-c40f8e911be443e2813ac3413ba28f76
Source dataset
uspto-grants-1996_10
Patent number
US05561141

Reaction notes

Loading…