Pyridine → N-(3-formylphenyl)methanesulfonamide

HRID 714465

Reaction equation

HRID 714465 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[O:9])[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[CH3:16][S:17](Cl)(=[O:19])=[O:18].C(OCC)(=O)C>ClCCl>[CH:8]([C:4]1[CH:3]=[C:2]([NH:1][S:17]([CH3:16])(=[O:19])=[O:18])[CH:7]=[CH:6][CH:5]=1)=[O:9]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 74366Benzaldehyde, 3-amino-

Product 1

HCID 2794787N-(3-formylphenyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.3 g (10.73 mmol) of 3-aminobenzenecarbaldehyde were initially charged in 30 ml of dichloromethane. 849 mg (10.73 mmol) of pyridine and 1.3 g (10.73 mmol) of methanesulfonyl chloride were added, and the mixture was then stirred at RT overnight. Ethyl acetate was added, and the reaction solution was washed in each case once with 1 N hydrochloric acid, water and saturated aqueous sodium bicarbonate solution. The organic phase was dried over sodium sulfate, filtered and evaporated. The residue was purified by column chromatography on silica gel 60 (mobile phase: dichloromethane/methanol 100/0→50/1).

Workup

  1. washthe reaction solution was washed in each case once with 1 N hydrochloric acid, water and saturated aqueous sodium bicarbonate solution
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel 60 (mobile phase: dichloromethane/methanol 100/0→50/1)

Sources & evidence

ORD record
ord-0ce1ef30f7a74835ba5753399bfa0386
Source dataset
uspto-grants-2015_11
Patent number
US09187428B2

Linked notes

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