2,5-Dimethoxyaniline → HCID 66731777, compound

HRID 1367771Notes

Reaction equation

HRID 1367771 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:4]=1[NH2:5].C([Li])CCC.Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36].[Cl-].[NH4+]>O1CCCC1.O1CCOCC1>[Si:35]([O:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][NH:5][C:4]1[CH:6]=[C:7]([O:10][CH3:11])[CH:8]=[CH:9][C:3]=1[O:2][CH3:1])([C:38]([CH3:39])([CH3:40])[CH3:41])([CH3:37])[CH3:36]

Participants

7

Reactant 4

HCID 76132,5-DimethoxyanilineHCID 25517Ammonium ChlorideHCID 86627057(16-Bromohexadecyloxy)-t-butyldimethylsilaneHCID 178418339Butyllithium

Product 1

HCID 66731777HCID 66731777, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

2,5-Dimethoxyaniline (352.3 mg) was dissolved in 20 ml of tetrahydrofuran, and then 2.3 ml of n-butyl lithium (1.0 M solution in hexane), 3 ml of a solution of (16-bromohexadecyloxy)-t-butyldimethylsilane in tetrahydrofuran, and 0.20 ml of 1,4-dioxane were added to this solution at 0° C. The reaction mixture was refluxed for 24 hours while stirring. Saturated ammonium chloride solution was added to the reaction mixture, which was then extracted three times with dichloromethane. The organic layer was washed with saline solution and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. Purification of the residue by silica gel chromatography (heptane:ethyl acetate=7:3) gave [16-(t-butyldimethylsilanyloxy)hexadecyl]-(2,5-dimethoxyphenyl)amine as a yellow oil at a 50% yield.

Workup

  1. temperatureThe reaction mixture was refluxed for 24 hours
  2. extractionwas then extracted three times with dichloromethane
  3. washThe organic layer was washed with saline solution
  4. dry with materialdried over magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customPurification of the residue by silica gel chromatography (heptane:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-92666152c73f4e68b19c89e26e7c9a04
Source dataset
uspto-grants-2011_02
Patent number
US07893304B2

Reaction notes

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