Phosphorus oxychloride → 2-Benzenesulfonylmethyl-5-methyl-[1,3,4]oxadiazole

HRID 602769Notes

Reaction equation

HRID 602769 reaction equation
[C:1]1([S:7]([CH2:10][C:11]([NH:13][NH:14][C:15](=[O:17])[CH3:16])=O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)=O>C(#N)C.O>[C:1]1([S:7]([CH2:10][C:11]2[O:17][C:15]([CH3:16])=[N:14][N:13]=2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 11402609acetic acid N'-(2-benzenesulfonyl-acetyl)-hydrazide

Product 1

HCID 114363472-Benzenesulfonylmethyl-5-methyl-[1,3,4]oxadiazoleYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 1.40 g (5.5 mmol) of acetic acid N′-(2-benzenesulfonyl-acetyl)-hydrazide in 50 mL of acetonitrile, 1.02 g (6.5 mmol, 1.2 eq) of phosphorus oxychloride were added, and the solution heated at reflux for 3 hours. The reaction mixture was diluted with water, extracted with EtOAc, the organic phase dried over Na2SO4, filtered and evaporated. Column chromatography on silica gel with EtOAc yielded 0.90 g (70%) of 2-benzenesulfonylmethyl-5-methyl-[1,3,4]oxadiazole as a white solid, MS: 239 (MH+).

Workup

  1. temperaturethe solution heated
  2. temperatureat reflux for 3 hours
  3. extractionextracted with EtOAc
  4. dry with materialthe organic phase dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-6c02b5803d884dd29c84c35b41951951
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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