1,4-Dioxane → HCID 68782331, compound

HRID 2266486Notes

Reaction equation

HRID 2266486 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([NH2:13])[CH:7]=1.C([O:17][C:18](=O)[CH:19]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=1)[C:20](=O)[CH2:21][CH3:22])C.O1CCOCC1.C([O-])(=O)C.[Na+]>O>[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]2[C:7]=1[C:18](=[O:17])[C:19]([CH2:24][C:25]1[CH:26]=[CH:27][C:28]([S:31]([CH3:34])(=[O:32])=[O:33])=[CH:29][CH:30]=1)=[C:20]([CH2:21][CH3:22])[NH:13]2

Participants

6

Reactant 4

HCID 312751,4-DioxaneHCID 517045Sodium AcetateHCID 66717604Methyl 2-(3-amino-4-chlorophenoxy)acetateHCID 68783725HCID 68783725, compound

Product 1

HCID 68782331HCID 68782331, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of (3-amino-4-chlorophenoxy)acetic acid methyl ester (0.54 g), 2-(4-methanesulfonylbenzyl)-3-oxopentanoic acid ethyl ester (0.78 g), polyphosphoric acid (2.5 mL) and dioxane (10 mL) was heated at 130° C. for 17 hours. The mixture was diluted with water (100 mL) and the pH of this solution adjusted to 4 by the addition of sodium acetate. The mixture was extracted with ethyl acetate and the combined extracts were washed with saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure to afford title compound as a honey coloured solid, 1.2 g.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe combined extracts were washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ed14f0964fa047b0b4bd5b1f1d80648c
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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