Diphenylamine → HCID 178419228, compound

HRID 648112Notes

Reaction equation

HRID 648112 reaction equation
[B:1](Cl)(Cl)[Cl:2].[C:5]1([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(Cl)Cl>[Cl-:2].[Cl-:2].[C:12]1([N:11]([BH2:1])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 11487DiphenylamineHCID 25135Boron Trichloride

Product 1

HCID 178419228HCID 178419228, compoundYield 27.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-70 °C

Procedure

To a solution of boron trichloride (4.5 g) in methylene chloride (3 ml), a solution of diphenylamine (6.5 g) in methylene chloride (12 ml) is added with cooling at -70° C., and the resultant mixture is stirred for 1 hour. The precipitated crystals are filtered at room temperature, washed with benzene, mixed with benzene (10 ml), and refluxed for 20 hours. After cooling, the reaction mixture is filtered to remove the insoluble material and evaporated under reduced pressure to remove the solvent. The residue is distilled under reduced pressure to give diphenylaminoborane dichloride (1.34 g) as an oil boiling at 117° to 120° C./0.9 mm Hg. M.P. 65°-69° C. [Gerrard, et al., J. Chem. Soc., 5168 (1960)].

Workup

  1. filtrationThe precipitated crystals are filtered at room temperature
  2. washwashed with benzene
  3. additionmixed with benzene (10 ml)
  4. temperaturerefluxed for 20 hours
  5. temperatureAfter cooling
  6. filtrationthe reaction mixture is filtered
  7. customto remove the insoluble material
  8. customevaporated under reduced pressure
  9. customto remove the solvent
  10. distillationThe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-598ca5664ca143e18fcab1177d31cec8
Source dataset
uspto-grants-1983_10
Patent number
US04410730

Reaction notes

Loading…