Methanol → 3-ethynylbenzenesulfonamide

HRID 238353Notes

Reaction equation

HRID 238353 reaction equation
C(=O)([O-])[O-].[K+].[K+].O1CCCC1.CO.C[Si]([C:18]#[C:19][C:20]1[CH:21]=[C:22]([S:26]([NH2:29])(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=1)(C)C>O>[C:19]([C:20]1[CH:21]=[C:22]([S:26]([NH2:29])(=[O:27])=[O:28])[CH:23]=[CH:24][CH:25]=1)#[CH:18]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 57458240HCID 57458240, compound

Product 1

HCID 469434133-ethynylbenzenesulfonamideYield 73.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under cooling in an ice bath, potassium carbonate (610 mg) was added to a tetrahydrofuran (30 mL) and methanol (70 mL) solution of 3-[(trimethylsilyl)ethynyl]benzenesulfonamide (11.1 g), and the obtained solution was then stirred at a room temperature for 12 hours. Thereafter, water was added to the reaction solution, and the solvent was then distilled away under a reduced pressure. Then, the residue was extracted with diethyl ether. The organic layer was washed with water and a saturated saline, and was then dried over anhydrous magnesium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (silica gel 60N, hexane:ethyl acetate=2:1 to 1:1), so as to obtain the title compound (5.84 g) in the form of a light brown solid.

Workup

  1. temperatureUnder cooling in an ice bath
  2. distillationthe solvent was then distilled away under a reduced pressure
  3. extractionThen, the residue was extracted with diethyl ether
  4. washThe organic layer was washed with water
  5. dry with materiala saturated saline, and was then dried over anhydrous magnesium sulfate
  6. concentrationfollowed by vacuum concentration
  7. customThe residue was purified by column chromatography (silica gel 60N, hexane:ethyl acetate=2:1 to 1:1)

Sources & evidence

ORD record
ord-02b7e093ae80413ea62b83638cbd8645
Source dataset
uspto-grants-2014_02
Patent number
US08642626B2

Reaction notes

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