Cyclopropanecarboxylic acid → 2-Benzenesulfonylmethyl-5-cyclopropyl-[1,3,4]oxadiazole

HRID 602773Notes

Reaction equation

HRID 602773 reaction equation
[C:1]1([S:7]([CH2:10][C:11]([NH:13][NH2:14])=[O:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:15]1([C:18](O)=O)[CH2:17][CH2:16]1>P(Cl)(Cl)(Cl)=O>[C:1]1([S:7]([CH2:10][C:11]2[O:12][C:18]([CH:15]3[CH2:17][CH2:16]3)=[N:14][N:13]=2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 15655Cyclopropanecarboxylic acidHCID 11378890Benzenesulfonyl-acetic acid hydrazide

Product 1

HCID 672669922-Benzenesulfonylmethyl-5-cyclopropyl-[1,3,4]oxadiazoleYield 41%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

To 3.0 g (14.0 mmol) of benzenesulfonyl-acetic acid hydrazide in 30 mL of phosphorus oxychloride, 1.47 g (17.0 mmol, 1.2 eq) of cyclopropanecarboxylic acid were added, and heated at reflux for 2 hours. The reaction mixture was very carefully poured onto ice, extracted with EtOAc, filtered and evaporated. Column chromatography on silica gel with EtOAc/heptane 2:1 yielded 1.49g (41%) of 2-benzenesulfonylmethyl-5-cyclopropyl-[1,3,4]oxadiazole as a white solid, MS: 265 (MH+).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. additionThe reaction mixture was very carefully poured onto ice
  4. extractionextracted with EtOAc
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-9e00ef55b21a4e8e8d37fbecd4efd09d
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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