Dimethylformamide → HCID 69781539, compound

HRID 2184320Notes

Reaction equation

HRID 2184320 reaction equation
Br[C:2]1([CH3:10])[CH:7]=[CH:6][C:5](Br)([CH3:8])[CH:4]=[CH:3]1.[C:11]([Cu])#[N:12].[CH3:14][N:15](C=O)C>>[C:14]([C:2]1([CH3:10])[CH:7]=[CH:6][C:5]([C:11]#[N:12])([CH3:8])[CH:4]=[CH:3]1)#[N:15]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 18374536HCID 18374536, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 69781539HCID 69781539, compoundYield 77%

Conditions

Temperature
50 °C

Procedure

A mixture of 1,4-dibromo-p-xylene (52.8 g, 0.2 mole), CuCN (53.4 g, 0.6 mole), and DMF (150 mL) is refluxed for about 19 hours. The yellow crystals formed are isolated by pouring the slurry into water and filtration. The crude product is stirred with a mixture of 500 mL of water and 100 mL of ethylenediamine until the yellow color has disappeared. The grey crystalline solid is added to a solution containing 200 mL of water, 50 mL of conc. HCl, and 50 g of ferric chloride hexahydrate and the resulting slurry stirred is warmed to about 50° C. for 30 minutes. The off-white crystalline solid is collected by filtration and recrystallized from 1.8 L of ethanol, yielding 24.0 g (77 percent yield) of 1,4-dicyano-p-xylene.

Workup

  1. temperatureis refluxed for about 19 hours
  2. customThe yellow crystals formed
  3. customare isolated
  4. additionby pouring the slurry
  5. filtrationinto water and filtration
  6. additionThe grey crystalline solid is added to a solution
  7. additioncontaining 200 mL of water, 50 mL of conc. HCl, and 50 g of ferric chloride hexahydrate
  8. stirringthe resulting slurry stirred
  9. filtrationThe off-white crystalline solid is collected by filtration
  10. customrecrystallized from 1.8 L of ethanol

Sources & evidence

ORD record
ord-9e8853f517e84c528661b01753951e92
Source dataset
uspto-grants-2005_05
Patent number
US06900285B2

Reaction notes

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