Methanol → HCID 20211717, compound

HRID 1906378Notes

Reaction equation

HRID 1906378 reaction equation
[C-]#N.[K+].[Cl-:4].[NH4+:5].[OH-].[NH4+:7].[C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=O)[CH3:9].[CH3:17]O>O>[ClH:4].[NH2:5][C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:17])[C:9]#[N:7]

Participants

7

Reactant 5

HCID 887MethanolHCID 7410AcetophenoneHCID 9032Potassium CyanideHCID 14923Ammonium HydroxideHCID 25517Ammonium Chloride

Product 1

HCID 20211717HCID 20211717, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a stirred solution of 3.8 g (0.058 mole) potassium cyanide in 7 ml water, a solution of 3.6 g (0.066 mole) ammonium chloride in 8 ml water was added. To the resulting mixture, 3.5 g (3.9 ml [0.10 mole]) ammonium hydroxide were added, followed by 7 g (0.058 mole) acetophenone dissolved in 10 ml methanol. The reaction mixture was heated at about 45°-55° C. for 18 hours. The black mixture was poured into water and extracted with methylene chloride. The methylene chloride extract was washed 4 times with water, dried over sodium sulfate, filtered and stripped. The residue was dissolved in ether. Hydrogen chloride gas was bubbled through the solution to precipitate 2 g of the above-identified hydrochloride salt, as a yellow solid.

Workup

  1. temperatureThe reaction mixture was heated at about 45°-55° C. for 18 hours
  2. extractionextracted with methylene chloride
  3. extractionThe methylene chloride extract
  4. washwas washed 4 times with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. dissolutionThe residue was dissolved in ether
  8. customHydrogen chloride gas was bubbled through the solution
  9. customto precipitate 2 g of the above-identified hydrochloride salt

Sources & evidence

ORD record
ord-a350793889b94224812425347490652b
Source dataset
uspto-grants-1987_03
Patent number
US04652556

Reaction notes

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