Chloride → Methyl 3-(benzyloxy)-5-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)benzoate

HRID 2098332Notes

Reaction equation

HRID 2098332 reaction equation
[C:1]([NH:4][NH:5][C:6]([C:8]1[CH:32]=[CH:31][C:11]([O:12][C:13]2[CH:14]=[C:15]([CH:20]=[C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:22]=2)[C:16]([O:18][CH3:19])=[O:17])=[CH:10][CH:9]=1)=[O:7])(=O)[CH3:2].[Cl-]>C1(C)C=CC=CC=1>[CH2:24]([O:23][C:21]1[CH:20]=[C:15]([CH:14]=[C:13]([O:12][C:11]2[CH:31]=[CH:32][C:8]([C:6]3[O:7][C:1]([CH3:2])=[N:4][N:5]=3)=[CH:9][CH:10]=2)[CH:22]=1)[C:16]([O:18][CH3:19])=[O:17])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 312ChlorideHCID 66972175Methyl 3-(4-(2-acetylhydrazinecarbonyl)phenoxy)-5-(benzyloxy)benzoate2×

Product 1

HCID 66972395Methyl 3-(benzyloxy)-5-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)benzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirring mixture of Methyl 3-(4-(2-acetylhydrazinecarbonyl)phenoxy)-5-(benzyloxy)benzoate (Intermediate 10) (32 g, 73.7 mmol, 1 equiv.) in toluene in a single necked round bottomed flask fitted with reflux condenser and anhydrous CaCl2 guard tube, thonyl chloride (10.5 g, 88.4 mmol, 1.2 equiv.) was added carefully. The reaction mixture was refluxed until the reaction was complete. After completion, the reaction mixture was poured onto ice and extracted twice with ethyl acetate. The combined organic extracts was washed with brine and dried over anhydrous sodium sulphate, filtered and concentrated under vacuum to give the title compound as yellow solid product (30 g).

Workup

  1. customfitted
  2. temperaturewith reflux condenser and anhydrous CaCl2 guard tube
  3. temperatureThe reaction mixture was refluxed until the reaction
  4. additionAfter completion, the reaction mixture was poured onto ice
  5. extractionextracted twice with ethyl acetate
  6. washThe combined organic extracts was washed with brine
  7. dry with materialdried over anhydrous sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-dc82125c886b4f9e8573f99224d81ea6
Source dataset
uspto-grants-2013_05
Patent number
US08450494B2

Reaction notes

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