Potassium Iodide → HCID 54485370, compound

HRID 2255811Notes

Reaction equation

HRID 2255811 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:15][CH:16]=[CH:17][CH2:18]Br.[I-].[K+].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:8]1([N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:15][CH:16]=[CH:17][CH2:18][N:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11487DiphenylamineHCID 131802-Butene, 1,4-dibromo-HCID 14798Sodium Hydroxide

Product 1

HCID 54485370HCID 54485370, compoundYield 39.3%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A vigorously stirred mixture of diphenylamine (150 g, 0.9 mol), 1,4-dibromobut-2-ene (104 g, 0.49 mol), potassium iodide (8 g, 0.05 mol), tetrabutylammonium bromide (7 g, 0.025 mol), sodium hydroxide (43 g, 1.06 mol) and 150 ml of water is warmed to 60° C. for five hours. The mixture is allowed to cool to room temperature. The solids formed are collected and washed with water. The residue is recrystallized from ethanol to give 69 grams (36% yield) of the title compound as a tan solid melting at 105°-107° C.

Workup

  1. temperatureto cool to room temperature
  2. customThe solids formed
  3. customare collected
  4. washwashed with water
  5. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-891a133642df4825a7548dc54cca4fbb
Source dataset
uspto-grants-1993_08
Patent number
US05240976

Reaction notes

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