Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 2-[3-(4-{[Benzyl(2-methyl-3-nitrophenyl)amino]methyl}phenoxy)phenoxy]ethanol

HRID 1370887Notes

Reaction equation

[CH2:1]([N:8]([C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([N+:39]([O-:41])=[O:40])[C:34]=1[CH3:42])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][CH2:25][O:26]C3CCCCO3)[CH:18]=2)=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CCO.C(OCC)(=O)C>[CH2:1]([N:8]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][C:17]2[CH:18]=[C:19]([CH:20]=[CH:21][CH:22]=2)[O:23][CH2:24][CH2:25][OH:26])=[CH:14][CH:15]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([N+:39]([O-:41])=[O:40])[C:34]=1[CH3:42])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 55 °C

Procedure

The product from Example 92A (0.480 g, 0.845 mmoles) in EtOH (2.0 mL) was treated with pyridinium p-toluenesulfonate (0.0106 g, 0.0422 mmoles) and heated at 55° C. for four hours. The reaction was diluted with ethyl acetate, washed with H2O, brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by chromatography on a pre-packed Biotage silica gel column (hexanes to 50% ethyl acetate:hexanes) to provide the title compound.

Workup

washwashed with H2O, brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationthe filtrate concentrated under reduced pressure
customThe residue was purified by chromatography on a pre-packed Biotage silica gel column (hexanes to 50% ethyl acetate:hexanes)

Sources & evidence

ORD record: ord-b3a80b3c5285430e8c5e6368e4c584b6
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06583180B2

Reaction notes

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