Dimethylformamide → HCID 18543000, compound

HRID 1276281Notes

Reaction equation

HRID 1276281 reaction equation
[CH3:1][N:2]([CH3:14])[C:3]1[CH:4]=[C:5](Br)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH3:15][N:16](C)C=O>O.ClCCl>[CH3:1][N:2]([CH3:14])[C:3]1[CH:4]=[C:5]([CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1)[C:15]#[N:16]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 18543036HCID 18543036, compound

Product 1

HCID 18543000HCID 18543000, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-dimethylamino-5-trifluoromethylbromobenzene (7.3 g) in N,N-dimethylformamide (20 mL) is added cuprous cyanide (2.7 g) and the reaction heated at reflux for 12 hours. The reaction is diluted with water (40 mL) and dichloromethane is added. The dichloromethane fraction is washed with concentrated ammonium hydroxide, then water. The solution is dried over anhydrous magnesium sulfate, filtered and concentrated to give a yellow solid which is recrystallized from hexanes to give a yellow solid, (4.7 g).

Workup

  1. temperaturethe reaction heated
  2. temperatureat reflux for 12 hours
  3. additionis added
  4. washThe dichloromethane fraction is washed with concentrated ammonium hydroxide
  5. dry with materialThe solution is dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a yellow solid which
  9. customis recrystallized from hexanes
  10. customto give a yellow solid, (4.7 g)

Sources & evidence

ORD record
ord-65dfa7ce450444d8b18b4256a6b114d6
Source dataset
uspto-grants-2000_12
Patent number
US06166028

Reaction notes

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