Aniline → 2-(1-Methyl-2-trimethylsilylethyl)phenylamine

HRID 1817919Notes

Reaction equation

HRID 1817919 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]([Si:11]([CH3:14])([CH3:13])[CH3:12])[CH:9]=[CH2:10].[Cl-].[Cl-].[Cl-].[Al+3].[Al].[OH-].[Na+]>O.C1(C)C=CC=CC=1>[CH3:10][CH:9]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH2:1])[CH2:8][Si:11]([CH3:14])([CH3:13])[CH3:12]

Participants

8

Reactant 5

HCID 6115AnilineHCID 14798Sodium HydroxideHCID 69808AllyltrimethylsilaneHCID 5359268AluminumHCID 6451240Aluminum(III) Chloride

Product 1

HCID 578833472-(1-Methyl-2-trimethylsilylethyl)phenylamineYield 3.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
255 °C

Procedure

17.7 g of aniline (0.19 mol), 50 g of allyltrimethylsilane (0.44 mol), 1.5 g of aluminum trichloride (0.01 mol) and 0.5 g of aluminum powder (0.02 mol) were mixed and stirred in an autoclave at 255° C. for 10 h. After cooling to room temperature, initially 100 ml of toluene and then 40 ml of a 40% strength solution of NaOH in water and 100 ml of water were added, and the mixture was stirred at 35° C. for 15 min. After cooling, the mixture was extracted with toluene, the extract was washed with water and dried over potassium carbonate and the solvent was removed under reduced pressure. Distillation (55° C.-60° C., 0.08 mbar) gave 1.4 g of 2-(1-methyl-2-trimethylsilylethyl)phenylamine [log P (pH 2.3)=3.05].

Workup

  1. temperatureAfter cooling to room temperature
  2. stirringthe mixture was stirred at 35° C. for 15 min
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted with toluene
  5. washthe extract was washed with water
  6. dry with materialdried over potassium carbonate
  7. customthe solvent was removed under reduced pressure
  8. distillationDistillation (55° C.-60° C., 0.08 mbar)

Sources & evidence

ORD record
ord-7eb2d34659cb4315ba173d3265979d53
Source dataset
uspto-grants-2009_10
Patent number
US07598389B2

Reaction notes

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