alpha-(5-Iodopentyl)-3,4-dimethoxy-alpha-[(4-methylphenyl)thio]benzeneacetonitrile → alpha-(3,4-Dimethoxypheny)1,3-dihydro-alpha-[(4-methylphenyl)thio]-1,3-dioxo-2H-isoindole-2-heptanenitrile

HRID 273987Notes

Reaction equation

HRID 273987 reaction equation
I[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].[C:28]1(=[O:38])[NH:32][C:31](=[O:33])[C:30]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:29]12.[K]>CN(C)C=O>[CH3:19][O:18][C:12]1[CH:11]=[C:10]([C:7]([S:20][C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:32]2[C:28](=[O:38])[C:29]3[C:30](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:31]2=[O:33])[C:8]#[N:9])[CH:15]=[CH:14][C:13]=1[O:16][CH3:17]

Participants

4

Reactant 2

HCID 19042083alpha-(5-Iodopentyl)-3,4-dimethoxy-alpha-[(4-methylphenyl)thio]benzeneacetonitrileHCID 24194345Phthalimide potassium salt

Product 1

HCID 10673372alpha-(3,4-Dimethoxypheny)1,3-dihydro-alpha-[(4-methylphenyl)thio]-1,3-dioxo-2H-isoindole-2-heptanenitrileYield 77.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6.12 g of α-(5-iodopentyl)-3,4-dimethoxy-α-[(4-methylphenyl)thio]benzeneacetonitrile and 2.22 g of potassium phthalimide and 50 mL of N,N-dimethylformamide is heated on a steam bath for 2 hours. The reaction solution is concentrated in vacuo and the residue is distributed between diethyl ether-water, with agitation. The organic layer is washed with 1N sodium hydroxide, followed by aqueous potassium bicarbonate. The solution is dried (sodium sulfate), and the volatiles removed in vacuo. Chromatography on silica gel, with gradient elution progressing from hexane to chloroform to methyl alcohol, affords 4.77 g of the desired product as a fluorescent oil.

Workup

  1. temperatureis heated on a steam bath for 2 hours
  2. concentrationThe reaction solution is concentrated in vacuo
  3. washThe organic layer is washed with 1N sodium hydroxide
  4. dry with materialThe solution is dried (sodium sulfate)
  5. customthe volatiles removed in vacuo

Sources & evidence

ORD record
ord-ccff48a9d655490ba6754034cb071ba9
Source dataset
uspto-grants-1995_02
Patent number
US05387685

Reaction notes

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