Sodium Hydroxide → HCID 53773737, compound

HRID 35930

Reaction equation

HRID 35930 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[O:10][CH2:11][CH:12]([CH2:14][O:15]S(C)(=O)=O)[N:13]=1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30](O)=[CH:29][CH:28]=2)=[CH:23][CH:22]=1.[OH-].[Na+].[Cl-].[NH4+]>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[O:10][CH2:11][CH:12]([CH2:14][O:15][C:30]2[CH:29]=[CH:28][C:27]([C:24]3[CH:23]=[CH:22][C:21]([Cl:20])=[CH:26][CH:25]=3)=[CH:32][CH:31]=2)[N:13]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 915894'-Chloro-4-biphenylolHCID 194240782-(2,6-Difluorophenyl)-4-methanesulfonyloxymethyl-2-oxazoline

Product 1

HCID 53773737HCID 53773737, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 200 mg (0.687 mmol.) of 2-(2,6-difluorophenyl)-4-methanesulfonyloxymethyl-2-oxazoline, 232 mg (1.00 mmol.) of 4-(4-chlorophenyl)phenol, 24 mg (1.0 mmol.) of sodium hydroxide and 3 ml of N,N-dimethylformamide was stirred at room temperature for 24 hours. After the reaction was completed, the reaction mixture was poured into 50 ml of a 10% aqueous solution of ammonium chloride and extracted twice with ethyl acetate. The residue was dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to give 50 mg of 2-(2,6-difluorophenyl)-4-{[4-(4-chlorophenyl) phenoxy]methyl}-2-oxazoline as a white solid (m.g. 99.5° C.).

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe residue was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-20d10e61da7843ba9fa3853e27ff73ce
Source dataset
uspto-grants-1995_05
Patent number
US05411979

Linked notes

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