Pyridine → N-(4-Ethynylphenyl)methanesulfonamide

HRID 2390812Notes

Reaction equation

HRID 2390812 reaction equation
[C:1]([C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1)#[CH:2].N1C=CC=CC=1.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C([O-])(O)=O.[Na+]>[C:1]([C:3]1[CH:9]=[CH:8][C:6]([NH:7][S:17]([CH3:16])(=[O:19])=[O:18])=[CH:5][CH:4]=1)#[CH:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 37600254-Ethynylaniline

Product 1

HCID 3749345N-(4-Ethynylphenyl)methanesulfonamideYield 89.2%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

step 1—To a solution of 4-ethynyl aniline (4.00 g, 34.00 mmol) DCM (60 mL) at 0° C. was added sequentially pyridine (3.32 mL, 40.8 mmol) and dropwise addition of methanesulfonyl chloride (3.17 mL, 40.80 mmol). The reaction was stirred and allowed to warm from 0° C. to RT over 3 h then poured into a saturated aqueous NaHCO3 (150 mL). The aqueous layer was separated and extracted with DCM (2×100 mL). The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified by SiO2 chromatography eluting with 20% EtOAc/hexanes to afford 5.92 g (88%) of N-(4-ethynyl-phenyl)-methanesulfonamide (80) as a solid.

Workup

  1. temperatureto warm from 0° C. to RT over 3 h
  2. customThe aqueous layer was separated
  3. extractionextracted with DCM (2×100 mL)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified by SiO2 chromatography
  9. washeluting with 20% EtOAc/hexanes

Sources & evidence

ORD record
ord-e341dc5bfba845e19692cfc6c9e400e8
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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