Sodium Iodide → 2,3-Dicyanonaphthalene

HRID 1090288

Reaction equation

HRID 1090288 reaction equation
Br[C:2]1[C:3](Br)=[C:4](Br)[C:5](Br)=[C:6]([CH3:9])[C:7]=1[CH3:8].[C:13](#[N:18])/[CH:14]=[CH:15]/[C:16]#[N:17].[I-].[Na+].S([O-])(O)=O.[Na+]>CN(C)C=O>[C:16]([C:15]1[C:14]([C:13]#[N:18])=[CH:8][C:7]2[C:6](=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:9]=1)#[N:17]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 177713,4,5,6-Tetrabromo-o-xyleneHCID 637930FumaronitrileHCID 23665763Sodium Bisulfite

Product 1

HCID 6012702,3-DicyanonaphthaleneYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To 0.1 mole of tetrabromoxylene, 0.17 mole of fumaronitrile, 0.66 mole of sodium iodide and 400 ml of anhydrous dimethylformamide were added and heated with stirring at 70 to 80° C. for 7 hours. The reaction solution was added to 800 g of ice water. To the deposited precipitate, about 15 g of sodium hydrogen sulfite was added and allowed to stand overnight. After filtration by suction and drying, while 2,3-dicyanonaphthalene was obtained by recrystallization from chloroform/ethanol in yield of 80%.

Workup

  1. temperatureheated
  2. waitto stand overnight
  3. filtrationAfter filtration by suction
  4. dry with materialdrying, while 2,3-dicyanonaphthalene
  5. customwas obtained by recrystallization from chloroform/ethanol in yield of 80%

Sources & evidence

ORD record
ord-9055e085ce8c43f884016c9c975cd909
Source dataset
uspto-grants-1992_01
Patent number
US05081236

Linked notes

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