Trimethylamine → HCID 129667418, compound

HRID 972382Notes

Reaction equation

HRID 972382 reaction equation
CN([C:4]1[C-:5]([CH3:9])[CH:6]=[CH:7][CH:8]=1)C.[CH-:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1.[Fe+2:15].[C-]#N.[K+].[CH3:19][N:20](C)C>O>[C:19]([CH2:9][C-:5]1[CH:4]=[CH:8][CH:7]=[CH:6]1)#[N:20].[CH-:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1.[Fe+2:15]

Participants

5

Reactant 3

HCID 1146TrimethylamineHCID 9032Potassium CyanideHCID 129690005HCID 129690005, compound

Product 1

HCID 129667418HCID 129667418, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

58 g (0.15 mole) of N,N-dimethylamino-methylferrocene methoidoide were added to a solution of 57 g (0.88 mole) of potassium cyanide in 570 ml of water and the mixture was heated to the boil, whereupon the solid dissolved. The evolution of trimethylamine started within a few minutes, while at the same time an oil which was volatile with steam separated out. After stirring for two hours under reflux, the mixture was cooled to room temperature, whereupon the oily product solidified. The solid was separated off and the residual solution was extracted with ether. The combined organic phases were washed with water and, after drying over sodium sulfate, concentrated under reduced pressure. The residue was recrystallized from 200 ml of hexane. In this way 26 g (76.9% of theory) of cyanomethylferrocene with a melting point of 82° to 83° C were obtained.

Workup

  1. temperaturethe mixture was heated to the boil, whereupon the solid
  2. dissolutiondissolved
  3. customseparated out
  4. temperatureunder reflux
  5. customThe solid was separated off
  6. extractionthe residual solution was extracted with ether
  7. washThe combined organic phases were washed with water
  8. dry with materialafter drying over sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was recrystallized from 200 ml of hexane

Sources & evidence

ORD record
ord-cd46e39cb1664bc581925df454de4c32
Source dataset
uspto-grants-1977_10
Patent number
US04053296

Reaction notes

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