Phosphoric Acid → HCID 129690005, compound

HRID 972381Notes

Reaction equation

HRID 972381 reaction equation
[CH3:1][N:2]([CH2:4]N(C)C)[CH3:3].P(=O)(O)(O)O.[OH-].[Na+].[CH-:15]1[CH:19]=[CH:18][CH:17]=[CH:16]1.[CH-:20]1[CH:24]=[CH:23][CH:22]=[CH:21]1.[Fe+2:25]>C(O)(=O)C.O>[CH3:1][N:2]([C:4]1[C-:19]([CH3:18])[CH:15]=[CH:16][CH:17]=1)[CH3:3].[CH-:20]1[CH:24]=[CH:23][CH:22]=[CH:21]1.[Fe+2:25]

Participants

7

Reactant 4

HCID 1004Phosphoric AcidHCID 5829N,N,N',N'-TetramethylmethanediamineHCID 7611Bis(eta-cyclopentadienyl) iron2×HCID 14798Sodium Hydroxide

Product 1

HCID 129690005HCID 129690005, compoundYield 83.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

173 g (1.69 moles) of bis-dimethylaminomethane were added, while cooling, to a solution of 173 g of phosphoric acid in 1,600 ml of glacial acetic acid, 185.6 g (1.0 mole) of ferrocene were then added and the mixture was warmed for 5 hours under a nitrogen atmosphere on a waterbath. The reaction mixture was then cooled to room temperature and diluted with 2,200 ml of water and unconverted ferrocene was removed by extraction with ether. The remaining reaction mixture was rendered alkaline by adding 480 g of sodium hydroxide, diluted with a further 800 ml of water and then extracted three times with ether. The organic phase was separated off, washed with water and, after drying over sodium sulfate, concentrated. 204 g (89% of theory) of N,N-dimethylamino-methylferrocene remained and were taken up in 215 ml of methanol. 215 ml (500 g) of methyl iodide were added to the resulting solution and the mixture was heated for 5 minutes on a boiling waterbath and, after cooling to room temperature, poured into 3,200 ml of ether. The product, which was initially obtained as an oil, crystallised on trituration. In this way, 323 g (83.9% of theory) of N,N-dimethylamino-methylferrocene methoiodide with a melting point of 213° C (decomposition) were obtained.

Workup

  1. additionwere then added
  2. temperaturethe mixture was warmed for 5 hours under a nitrogen atmosphere on a waterbath
  3. customwas removed by extraction with ether
  4. customThe remaining reaction mixture
  5. extractionextracted three times with ether
  6. customThe organic phase was separated off
  7. washwashed with water
  8. dry with materialafter drying over sodium sulfate
  9. concentrationconcentrated
  10. addition215 ml (500 g) of methyl iodide were added to the resulting solution
  11. temperaturethe mixture was heated for 5 minutes on a boiling waterbath
  12. temperatureafter cooling to room temperature
  13. additionpoured into 3,200 ml of ether
  14. customThe product, which was initially obtained as an oil
  15. customcrystallised on trituration

Sources & evidence

ORD record
ord-5fa4a960d0bd4212a4797e948dd0c2cc
Source dataset
uspto-grants-1977_10
Patent number
US04053296

Reaction notes

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