18-Crown-6 → HCID 30849053, compound

HRID 602818Notes

Reaction equation

HRID 602818 reaction equation
Cl[CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:4]=1.[C:14]1([S:20]([O-:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Na+].C1OCCOCCOCCOCCOCCOC1>C(#N)C>[C:14]1([S:20]([CH2:2][C:3]2[O:7][N:6]=[C:5]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[N:4]=2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 9667145-(Chloromethyl)-3-phenyl-1,2,4-oxadiazoleHCID 2723840Benzenesulfinic acid, sodium salt2×

Product 1

HCID 30849053HCID 30849053, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 525 mg (2.7 mmol) of 5-chloromethyl-3-phenyl-[1,2,4]oxadiazole in acetonitrile at RT, 465 mg (2.8 mmol, 1.05 eq) of sodium benzenesulfinate and 143 mg (0.5 mmol, 0.2 eq) of 18-crown-6 were added. Stirring was continued overnight, and an additional 50 mg (0.3 mmol, 0.12 eq) of sodium benzenesulfinate were added and the reaction mixture was allowed to stirr for one further hour. The solvent was evaporated and the resulting oil was taken up in EtOAc, washed with a saturated NaHCO3 solution. The organic phase was dried over Na2SO4, filtered and evaporated. Column chromatography on silica gel (heptane/EtOAc 8:2) yielded 622 mg (77%) of 5-benzenesulfonylmethyl-3-phenyl-[1,2,4]oxadiazole as a white solid, MS: 301 (MH+).

Workup

  1. customThe solvent was evaporated
  2. washwashed with a saturated NaHCO3 solution
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-6abd7554c5f54a5ca15074b745e13ebd
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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