2-Methoxyethanol → N-benzyl-N-{4-[3-(2-methoxyethoxy)phenoxy]benzyl}-N-(2-methyl-3-nitrophenyl)amine

HRID 1370834Notes

Reaction equation

HRID 1370834 reaction equation
[CH2:1]([N:8]([CH2:19][C:20]1[CH:33]=[CH:32][C:23]([O:24][C:25]2[CH:26]=[C:27]([OH:31])[CH:28]=[CH:29][CH:30]=2)=[CH:22][CH:21]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:10]=1[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:53][O:54][CH2:55][CH2:56]O>C1COCC1.C(OCC)(=O)C>[CH2:1]([N:8]([CH2:19][C:20]1[CH:33]=[CH:32][C:23]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:56][CH2:55][O:54][CH3:53])[CH:26]=2)=[CH:22][CH:21]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:10]=1[CH3:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 80192-MethoxyethanolHCID 11776TriphenylphosphineHCID 185122603-(4-{[Benzyl(2-methyl-3-nitrophenyl)amino]methyl}phenoxy)phenol

Product 1

HCID 18511918N-benzyl-N-{4-[3-(2-methoxyethoxy)phenoxy]benzyl}-N-(2-methyl-3-nitrophenyl)amine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product from Example 61F (0.100 g, 0.227 mmoles), polystyrene supported triphenylphosphine (0.151 g, 0.454 mmoles, 3 mmoles P/g resin), and di-t-butylazodicarboxylate (0.079 g, 0.341 mmoles) in THF (2 mL) were treated with 2-methoxyethanol (0.022 g, 0.284 mmoles). The reaction mixture was shaken overnight at room temperature. The mixture was diluted with ethyl acetate, washed with H2O, brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure to provide the title compound without further purification.

Workup

  1. washwashed with H2O, brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-8b7acc425c124e9c854b568d42fc870c
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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