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

HRID 273985Notes

Reaction equation

HRID 273985 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([S:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].[Na+].Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][Cl:30]>CN(C)C=O>[Cl:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][C:11]([S:14][C:15]1[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=1)([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:12]#[N:13]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 960701-Bromo-5-chloropentaneHCID 105421673,4-Dimethoxy-alpha[(4-methylphenyl)thio]benzeneacetonitrile

Product 1

HCID 10573255alpha-(5-Chloropentyl)-3,4-dimethoxy-alpha-[(4-methylphenyl)-thio]benzeneacetonitrileYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 5.00 g of 3,4-dimethoxy-α-[(4-methylphenyl)thio]benzeneacetonitrile in 50 mL of N,N-dimethylformamide, under an argon atmosphere, is added 0.73 g of 60% sodium hydride in oil. After 1.5 hours, 4.65 g of 1-bromo-5-chloropentane is added to the resulting solution and stirring continued for 3 hours. The reaction is poured into ice water, and twice extracted with diethyl ether. The combined organic extracts are dried (magnesium sulfate), and concentrated in vacuo to give a golden oil. Purification by chromatography on a silica gel column using diethyl ether/hexane (2:3), affords 6.07 g of the desired product as a colorless oil.

Workup

  1. waitcontinued for 3 hours
  2. extractiontwice extracted with diethyl ether
  3. dry with materialThe combined organic extracts are dried (magnesium sulfate)
  4. concentrationconcentrated in vacuo
  5. customto give a golden oil
  6. customPurification by chromatography on a silica gel column

Sources & evidence

ORD record
ord-d26bf99d644c4db8aa1181f04dc9144f
Source dataset
uspto-grants-1995_02
Patent number
US05387685

Reaction notes

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