Sodium Iodide → HCID 15766431, compound

HRID 975176Notes

Reaction equation

HRID 975176 reaction equation
[C:1]1([N:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=3)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S1(CCCC1)(=O)=O.[I-].[Na+].C[Si](C)(C)Cl>O>[C:1]1([N:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]3[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=3)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 31347SulfolaneHCID 11211174HCID 11211174, compound

Product 1

HCID 15766431HCID 15766431, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
120 °C

Procedure

A mixture of 38.5 g of the 1-(4-diphenylaminophenyl)-2-(4-methoxyphenyl)ethane prepared in Synthesis Example 1-2, 200 ml of sulfolane, and 45 g of sodium iodide was stirred in a four-neck flask at 120° C. to obtain a solution. The thus obtained solution was cooled to 60° C., and 2 ml of distilled water was added to the solution. 32.6 g of trimethylchlorosilane was then added dropwise to the above solution over a period of 30 minutes. Thus, the reaction was carried out at 60° to 70° C. for three hours. The thus obtained reaction mixture was poured into 500 ml of water, whereby a brown tar was obtained. The thus obtained tar was washed with 200 ml of water several times, and dissolved in 300 ml of toluene, whereby a brown toluene solution was obtained. The thus obtained toluene solution was washed twice with 100 ml of a saturated aqueous solution of sodium sulfite, whereby a transparent toluene solution of light yellow in color was obtained. After the thus obtained transparent toluene solution was dried over anhydrous magnesium sulfate, a solvent was distilled away. The thus obtained product was subjected to chromatography using a silica gel and toluene, whereby 31.4 g of 1-(4-diphenylaminophenyl)- 2-(4-hydroxyphenyl)ethane was obtained as an oily material.

Workup

  1. customto obtain a solution
  2. temperatureThe thus obtained solution was cooled to 60° C.
  3. customThe thus obtained reaction mixture
  4. customwas obtained
  5. washThe thus obtained tar was washed with 200 ml of water several times
  6. dissolutiondissolved in 300 ml of toluene
  7. customwhereby a brown toluene solution was obtained
  8. washThe thus obtained toluene solution was washed twice with 100 ml of a saturated aqueous solution of sodium sulfite, whereby a transparent toluene solution of light yellow in color
  9. customwas obtained
  10. dry with materialAfter the thus obtained transparent toluene solution was dried over anhydrous magnesium sulfate
  11. distillationa solvent was distilled away

Sources & evidence

ORD record
ord-7fd80841804f451da440d6fa746fa02a
Source dataset
uspto-grants-1997_03
Patent number
US05608010

Reaction notes

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