Potassium Iodide → HCID 14968342, compound

HRID 249206Notes

Reaction equation

HRID 249206 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:15](Br)[CH:16]=[CH2:17].[I-].[K+].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:15]([N:14]([CH2:5][CH:4]=[CH2:3])[C:11]1[CH:12]=[CH:13][C:8]([N:7]([CH2:6][CH:1]=[CH2:2])[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:9][CH:10]=1)[CH:16]=[CH2:17]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7564N-Phenyl-p-phenylenediamineHCID 7841Allyl bromideHCID 14798Sodium Hydroxide

Product 1

HCID 14968342HCID 14968342, compound

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Conditions

Temperature
80 °C

Procedure

A well-stirred intimate mixture of N-phenyl-p-phenylenediamine (10 g, 0.054 mol), allyl bromide (16 ml, 0.18 mol), potassium iodide (1 g, 0.006 mol) and tetrabutylammonium bromide (1 g, 0.003 mol) is treated with an aqueous solution of sodium hydroxide (7.2 g, 0.18 mol). The mixture is heated to 80° C. for five hours. The mixture is then cooled and extracted with diethyl ether. The organic layer is dried over anhydrous magnesium sulfate and concentrated to an oil. The oil is chromatographed (silica gel; hexane:ethyl acetate) to give the title compound in a yield of 13.1 g (80%) as a yellow oil.

Workup

  1. temperatureThe mixture is then cooled
  2. extractionextracted with diethyl ether
  3. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  4. concentrationconcentrated to an oil
  5. customThe oil is chromatographed (silica gel; hexane:ethyl acetate)

Sources & evidence

ORD record
ord-42bfc8086b12429689353edc69404666
Source dataset
uspto-grants-1993_05
Patent number
US05213699

Reaction notes

Loading…