Dimethylamine → HCID 178427810, compound

HRID 36121Notes

Reaction equation

HRID 36121 reaction equation
[CH3:1][NH:2][CH3:3].[Cl-:4].[Cl-].[CH3:6][C:7]1([Zr+2:13][C:14]2([CH3:20])[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15]2)[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8]1>C1(C)C=CC=CC=1>[CH3:6][C:7]1([Zr+2:13][C:14]2([CH3:20])[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15]2)[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8]1.[Cl-:4].[CH3:1][N-:2][CH3:3]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 178427809HCID 178427809, compound

Product 1

HCID 178427810HCID 178427810, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-10 °C

Procedure

Into a 500 ml glass reactor thoroughly purged with nitrogen were charged 100 ml of dry hexane and n-butyl lithium (hexane solution of 1.62 M, 15.6 ml), and they were stirred at -10° C. To the reaction liquid was added 1.25 g of dimethylamine at -10° C. and stirred for 30 min. The temperature of the reaction system was raised to 0° C. After the reaction of 1 hour, nitrogen was blown into the reaction system to remove the residual dimethylamine. To the reaction liquid was dropwise added 200 ml of a toluene solution containing 3.66 g of bis(1,3-dimethylcyclopentadienyl) zirconium (IV)-dichloride over a period of 30 min, and the reaction liquid was stirred at 0° C. The temperature of the reaction system was raised to room temperature. After the reaction of 1 hour, the reaction liquid was heated at 95° C. for 6 hours, and the produced salt was removed by means of filtration. The filtrate was concentrated (about 20 ml). The precipitated solid was filtered, and the obtained brown solid was purified by means of sablimation (200° C. 0.5 mmHg), to obtain 0.60 g of a crystal of bis(1,3-dimethylcyclopentadienyl)-zirconium (IV)-(dimethylamide)chloride (yield: 18%).

Workup

  1. customInto a 500 ml glass reactor thoroughly purged with nitrogen
  2. additionwere charged 100 ml of dry hexane and n-butyl lithium (hexane solution of 1.62 M, 15.6 ml), and they
  3. customTo the reaction liquid
  4. stirringstirred for 30 min
  5. temperatureThe temperature of the reaction system was raised to 0° C
  6. customAfter the reaction of 1 hour, nitrogen
  7. customto remove the residual dimethylamine
  8. customTo the reaction liquid
  9. customthe reaction liquid
  10. stirringwas stirred at 0° C
  11. temperatureThe temperature of the reaction system was raised to room temperature
  12. customAfter the reaction of 1 hour
  13. customthe reaction liquid
  14. temperaturewas heated at 95° C. for 6 hours
  15. customthe produced salt was removed by means of filtration
  16. concentrationThe filtrate was concentrated (about 20 ml)
  17. filtrationThe precipitated solid was filtered
  18. customthe obtained brown solid was purified by means of sablimation (200° C. 0.5 mmHg)

Sources & evidence

ORD record
ord-ebd77233697749b5882323ee4079ae12
Source dataset
uspto-grants-1995_05
Patent number
US05412128

Reaction notes

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