1-Bromo-3-chloropropane → alpha-(3-Chloropropyl)-3,4-dimethoxy-alpha-[(4-methylphenyl)-thio]benzeneacetonitrile

HRID 273977Notes

Reaction equation

HRID 273977 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][Cl:28]>CS(C)=O>[Cl: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 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 105421673,4-Dimethoxy-alpha[(4-methylphenyl)thio]benzeneacetonitrile

Product 1

HCID 10738259alpha-(3-Chloropropyl)-3,4-dimethoxy-alpha-[(4-methylphenyl)-thio]benzeneacetonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2.39 g of 3,4-dimethoxy-α-[(4-methylphenyl)thio]benzeneacetonitrile in 21 mL of dimethyl sulfoxide, under an argon atmosphere with stirring, is added 0.336 g of 60% sodium hydride in oil. This mixture is stirred for 1.5 hours. To the resulting solution is added 1.32 g of 1-bromo-3-chloropropane and this reaction mixture is stirred for 3 hours and is next poured into 100 mL of ice water. This mixture is twice extracted with diethyl ether and the combined organic extracts dried with magnesium sulfate. The organic solution is filtered, and concentrated in vacuo to give the desired compound as a golden oil.

Workup

  1. stirringthis reaction mixture is stirred for 3 hours
  2. extractionThis mixture is twice extracted with diethyl ether
  3. dry with materialthe combined organic extracts dried with magnesium sulfate
  4. filtrationThe organic solution is filtered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-623e6cf846ba4185a67a3d0837fbe1b2
Source dataset
uspto-grants-1995_02
Patent number
US05387685

Reaction notes

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