(Phenylthio)acetyl chloride → Methyl 5-[(phenylthio)methyl]-1,2,4-oxadiazole-3-carboxylate

HRID 602778Notes

Reaction equation

HRID 602778 reaction equation
[CH3:1][O:2][C:3](=[O:8])[C:4]([NH2:7])=[N:5][OH:6].[C:9]1([S:15][CH2:16][C:17](Cl)=O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1COCC1>[CH3:1][O:2][C:3]([C:4]1[N:7]=[C:17]([CH2:16][S:15][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:6][N:5]=1)=[O:8]

Participants

4

Reactant 2

HCID 4063350(Phenylthio)acetyl chlorideHCID 76223575HCID 76223575, compound

Product 1

HCID 67266859Methyl 5-[(phenylthio)methyl]-1,2,4-oxadiazole-3-carboxylateYield 54.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

300 mg (2.54 mmol) of amino-hydroxyimino-acetic acid methyl ester and 428 mg (2.29 mmol, 0.9 eq) of phenylsulfanyl-acetyl chloride were stirred in 10 mL of THF at RT for 1 hour. The solvent was evaporated, the residue dissolved in dioxane, and the reaction mixture was heated at reflux over night in the presence of molecular sieves. Filtration, concentration under vacuum and column chromatography over silica gel with EtOAc/heptane 1:1 yielded 310 mg (49%) of 5-phenylsulfanylmethyl-[1,2,4]oxadiazole-3-carboxylic acid methyl ester as light yellow oil, MS: 268 (MNH4+).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in dioxane
  3. temperaturethe reaction mixture was heated
  4. temperatureat reflux over night in the presence of molecular sieves
  5. filtrationFiltration, concentration under vacuum and column chromatography over silica gel with EtOAc/heptane 1:1

Sources & evidence

ORD record
ord-e7b1ba8aa443446182d0db869b66e20e
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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