Sodium Iodide → 2,3-Dicyanonaphthalene

HRID 1493438

Reaction equation

HRID 1493438 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

Procedure

To 0.1 mol of tetrabromoxylene were added 0.17 mol of fumaronitrile, 0.66 mol of sodium iodide and 400 ml of anhydrous dimethylformamide, and the mixture was stirred under heating at 70° to 80° C. for 7 hours. The reaction mixture was added to 800 g of ice-water, and to the resultant precipitate was added about 15 g of sodium hydrogen sulfite and the mixture was left to stand overnight. Subsequently, the mixture was filtered and dried, followed by recrystallization from chloroform/ethanol, to give white 2,3-dicyanonaphthalene. The yield was 80%.

Workup

  1. temperatureunder heating at 70° to 80° C. for 7 hours
  2. waitthe mixture was left
  3. filtrationSubsequently, the mixture was filtered
  4. customdried
  5. customfollowed by recrystallization from chloroform/ethanol

Sources & evidence

ORD record
ord-e0e2acd1e5994ea8823a6809fbceb207
Source dataset
uspto-grants-1991_06
Patent number
US05021563

Linked notes

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