Dimethyl Sulfoxide → HCID 10014125, compound

HRID 1590210Notes

Reaction equation

HRID 1590210 reaction equation
CS(C)=O.[CH2:5]1[O:13][C:12]2[C:7](=[C:8]([CH2:14][C:15]#[N:16])[CH:9]=[CH:10][CH:11]=2)[O:6]1.[CH2:17](Br)[CH2:18][CH2:19][CH2:20][CH3:21].[OH-].[Na+]>O>[CH2:5]1[O:13][C:12]2[C:7](=[C:8]([CH:14]([C:15]#[N:16])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:9]=[CH:10][CH:11]=2)[O:6]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 80571-BromopentaneHCID 14798Sodium HydroxideHCID 14943511(2H-1,3-Benzodioxol-4-yl)acetonitrile

Product 1

HCID 10014125HCID 10014125, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into 5 ml of dimethylsulfoxide, was added 0.26 g (1.6 mmol) of 2,3-methylenedioxyphenylacetonitrile, then, 0.24 g (1.6 mmol) of n-pentyl bromide and a 50% aqueous solution of sodium hydroxide were added dropwise thereinto simultaneously under cooling with ice. After 30-minute stirring at room temperature, the mixutre was added with water and extracted with ether. The ether extract was dried over magnesium chloride and then the solvent was evaporated off to obtain 0.30 g of oily 1-(2,3-methylenedioxyphenyl)hexane carbonitrile.

Workup

  1. temperaturesimultaneously under cooling with ice
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. dry with materialwas dried over magnesium chloride
  5. customthe solvent was evaporated off

Sources & evidence

ORD record
ord-3608f37ee8fd48a094aa0dbaf8df9384
Source dataset
uspto-grants-1993_04
Patent number
US05202351

Reaction notes

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