Water → HCID 69212300, compound

HRID 2251327Notes

Reaction equation

HRID 2251327 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[C:18]([CH3:25])[CH:17]=2)=[C:12]([CH:26]([CH3:28])[CH3:27])[O:11][N:10]=1.O.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]1[C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([CH3:25])[CH:17]=2)=[C:12]([CH:26]([CH3:28])[CH3:27])[O:11][N:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 69209868HCID 69209868, compound

Product 1

HCID 69212300HCID 69212300, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-(2,6-dichlorophenyl)-5-isopropyl-4-[(3-methyl-4-nitrophenoxy)methyl]isoxazole (0.36 g, 0.86 mmol) in ethanol (3 mL) was treated with tni(II)chloride (0.71 g, 3.2 mmol) and refluxed overnight. Water (15 mL) was added and the pH adjusted to 10-11 with solid sodium carbonate. The product was then extracted with chloroform; the combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered, and condensed to a residue which was chromatographed on silica gel using 50% ethyl acetateihexane. Yield=0.24 g. (72%) of 4-{[3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl]methoxy}-2-methylphenylamine.

Workup

  1. temperaturerefluxed overnight
  2. extractionThe product was then extracted with chloroform
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customcondensed to a residue which
  7. customwas chromatographed on silica gel using 50% ethyl acetateihexane

Sources & evidence

ORD record
ord-9273a63611e14350aab8ea7ab5e7aafe
Source dataset
uspto-grants-2008_01
Patent number
US07319109B2

Reaction notes

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