Diphenylamine → HCID 22599334, compound

HRID 1031853Notes

Reaction equation

HRID 1031853 reaction equation
[Ti:1](Cl)(Cl)(Cl)Cl.[C:6]1([N-:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Li+].[C:20]1([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1(C)C=CC=CC=1>[C:13]1([N-:12][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1.[C:27]1([N-:26][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1.[C:13]1([N-:12][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1.[C:13]1([N-:12][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1.[Ti+4:1]

Participants

5

Reactant 3

HCID 11487DiphenylamineHCID 24193Titanium TetrachlorideHCID 11137635HCID 11137635, compound

Product 1

HCID 22599334HCID 22599334, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-20 °C

Procedure

The same apparatus described in Step (1) of Example 1-E is used in this procedure. The 250 ml dropping funnel is charged with toluene, 50 ml, and titanium tetrachloride, 2.4 ml (0.022 mole). This is added dropwise to the flask containing lithium diphenylamide which is maintained at -20° C. during the addition while stirring magnetically. Total addition time is 30 minutes. The mixture is warmed to room temperature and then refluxed for 2 hours. All volatiles are removed under vacuum to give a deep red oily residue. Unreacted diphenylamine is sublimed from the oil under reduced pressure at 120° C. to give a red solid: Extraction of the solid with hexane, 50 ml, followed by solvent volume reduction under vacuum then cooling to -30° C. yields red crystals of titanium tetrakis(diphenylamide).

Workup

  1. additionThis is added dropwise to the flask
  2. temperatureThe mixture is warmed to room temperature
  3. temperaturerefluxed for 2 hours
  4. customAll volatiles are removed under vacuum
  5. customto give a deep red oily residue
  6. customis sublimed from the oil under reduced pressure at 120° C.
  7. customto give a red solid
  8. extractionExtraction of the solid with hexane, 50 ml
  9. temperaturethen cooling to -30° C.

Sources & evidence

ORD record
ord-7093cf0b515e4218ae8a7587eaf4ce2f
Source dataset
uspto-grants-1990_09
Patent number
US04956323

Reaction notes

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