Sodium Iodide → HCID 58755318, compound

HRID 2251330Notes

Reaction equation

HRID 2251330 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[CH2:26]Cl)[O:5][CH2:6][C:7]1[C:8]([C:15]2[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:22])=[N:9][O:10][C:11]=1[CH:12]([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[OH:36][C:37]1[CH:46]=[CH:45][C:40]([C:41]([O:43][CH3:44])=[O:42])=[CH:39][CH:38]=1>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([O:5][CH2:6][C:7]2[C:8]([C:15]3[C:16]([Cl:22])=[CH:17][CH:18]=[CH:19][C:20]=3[Cl:21])=[N:9][O:10][C:11]=2[CH:12]([CH3:14])[CH3:13])[CH:23]=[CH:24][C:25]=1[CH2:26][O:36][C:37]1[CH:38]=[CH:39][C:40]([C:41]([O:43][CH3:44])=[O:42])=[CH:45][CH:46]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 69212253HCID 69212253, compound

Product 1

HCID 58755318HCID 58755318, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-{[3-chloro-4-(chloromethyl)phenoxy]methyl}-3-(2,6-dichlorophenyl)-5-isopropylisoxazole (50 mg, 112 μmol), potassium carbonate (16.9 mg, 122 μmol), sodium iodide (18.3 mg, 110 μmol), and methyl 4-hydroxybenzoate (16.7 mg, 110 μmol) in dimethylformamide (0.6 mL) was stirred at ambient temperature overnight. The mixture was filtered, condensed to a residue, and was chromatographed on silica gel eluting with 33% ethyl acetate/hexanes. Yield=41 mg (65%) of methyl 4-[(2-chloro-4-{[3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl]methoxy}benzyl)oxy]-benzoate.

Workup

  1. filtrationThe mixture was filtered
  2. customcondensed to a residue
  3. customwas chromatographed on silica gel eluting with 33% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-6590e7fec0b749a49ff9db849dcbf9ef
Source dataset
uspto-grants-2008_01
Patent number
US07319109B2

Reaction notes

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