4-Toluenesulfonyl chloride → 1-Methyl-1-[5-[2-[[4-(methylthio)phenyl]amino]-4-pyridyl]-1,3,4-oxadiazol-2-yl]ethyl acetate

HRID 452772Notes

Reaction equation

HRID 452772 reaction equation
[C:1]([O:4][C:5]([CH3:28])([CH3:27])[C:6]([NH:8][NH:9][C:10](=[O:26])[C:11]1[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([S:24][CH3:25])=[CH:20][CH:19]=2)[CH:12]=1)=O)(=[O:3])[CH3:2].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>N1C=CC=CC=1>[C:1]([O:4][C:5]([CH3:28])([C:6]1[O:26][C:10]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([S:24][CH3:25])=[CH:20][CH:19]=3)[CH:12]=2)=[N:9][N:8]=1)[CH3:27])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 686646781,1-Dimethyl-2-[2-[2-[[4-(methylthio)phenyl]amino]isonicotinoyl]hydrazino]-2-oxoethyl acetate

Product 1

HCID 686643731-Methyl-1-[5-[2-[[4-(methylthio)phenyl]amino]-4-pyridyl]-1,3,4-oxadiazol-2-yl]ethyl acetateYield 40.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1,1-dimethyl-2-[2-[2-[[4-(methylthio)phenyl]amino]isonicotinoyl]hydrazino]-2-oxoethyl acetate (624 mg, 1.55 mmol) and p-toluenesulfonyl chloride (888 mg, 4.66 mmol) in pyridine (15 mL) was stirred at 90-95° C. overnight. After cooling, the reaction mixture was concentrated under reduced pressure. The residue was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=10/1-0/1) and recrystallized from hexane/ethyl acetate to give the title compound (240 mg, yield 40%) as yellow crystals.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=10/1-0/1)
  8. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-3be7b0a31adc45e8bd23e1cfe89badc0
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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