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

HRID 75972Notes

Reaction equation

HRID 75972 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].S(Cl)(Cl)=O>C1(C)C=CC=CC=1.O>[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

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 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)benzoateYield 97.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a stirring solution of Methyl 3-[4-(2-acetylhydrazinecarbonyl)phenoxy]-5-(benzyloxy)benzoate (32 g) (Intermediate 9) in dry toluene was added thionyl chloride (10.5 g) drop wise at room temperature under nitrogen atmosphere. The reaction was refluxed and monitored by TLC. After completion of the reaction, reaction mixture was diluted with water and extracted with EtOAc. All organic layers were combined and washed with saturated sodium bicarbonate solution, water, and brine, dried over anhydrous sodium sulphate, filtered and concentrated under vacuum to get crude pale yellow solid (30 g). The crude compound was purified by solvent trituration.

Workup

  1. temperatureThe reaction was refluxed
  2. customAfter completion of the reaction, reaction mixture
  3. extractionextracted with EtOAc
  4. washwashed with saturated sodium bicarbonate solution, water, and brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7f6f4487f5dd4126ac1f9525c854fc1b
Source dataset
uspto-grants-2014_09
Patent number
US08835469B2

Reaction notes

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