Indene → HCID 178484298, compound

HRID 1613831Notes

Reaction equation

HRID 1613831 reaction equation
[CH3:1][N-:2][CH3:3].[CH3:4][N-:5][CH3:6].[CH3:7][N-:8][CH3:9].C[N-]C.[Ti+4:13].[CH2:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15]1>C1(C)C=CC=CC=1>[CH3:1][N-:2][CH3:3].[CH3:4][N-:5][CH3:6].[CH3:7][N-:8][CH3:9].[CH:14]1([Ti+3:13])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15]1

Participants

4

Reactant 2

HCID 7219IndeneHCID 123185Methanamine, N-methyl-, titanium(4+) salt (4:1)

Product 1

HCID 178484298HCID 178484298, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 250 mL Schlenk flask is charged with toluene, 75 mL, and titanium tetrakis(dimethylamide), 2.35 g (10.48 mmole). The mixture is stirred magnetically throughout the procedure. Freshly degassed indene (nitrogen sparged) is added to the Schlenk flask at room temperature in excess, 2.44 mL (20.96 mmole). The mixture is refluxed at least 24 hours giving a blood red solution. All volatiles are removed under vacuum at room temperature leaving a deep red, oily residue. The residue is transferred in a minimum of hexane to a micro scale distillation apparatus and distilled under vacuum. A viscous red oil distills at 60° C. (0.025 mm Hg) which is identified by nuclear magnetic resonance (NMR) as indenyltitanium tris(dimethylamide). The yield is 70% by this method of preparation.

Workup

  1. temperatureThe mixture is refluxed at least 24 hours
  2. customgiving a blood red solution
  3. customAll volatiles are removed under vacuum at room temperature
  4. customleaving a deep red, oily residue
  5. distillationThe residue is transferred in a minimum of hexane to a micro scale distillation apparatus
  6. distillationdistilled under vacuum
  7. distillationA viscous red oil distills at 60° C. (0.025 mm Hg) which
  8. customThe yield is 70% by this method of preparation

Sources & evidence

ORD record
ord-8bea02ef4d0c48528faa8b914048ff06
Source dataset
uspto-grants-1993_03
Patent number
US05194532

Reaction notes

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