Pyridine → N-(4-methoxyphenyl)cyanomethanesulfonamide

HRID 1027588Notes

Reaction equation

HRID 1027588 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.N1C=CC=CC=1.[C:16]([CH2:18][S:19](Cl)(=[O:21])=[O:20])#[N:17].[OH-].[Na+]>C(#N)C.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][S:19]([CH2:18][C:16]#[N:17])(=[O:21])=[O:20])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 7732P-AnisidineHCID 14798Sodium HydroxideHCID 13142426Cyanomethanesulfonyl chloride

Product 1

HCID 61794435N-(4-methoxyphenyl)cyanomethanesulfonamideYield 18.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of para-anisidine (1.95 g) in acetonitrile (25 ml) at 15° C. under argon atmosphere was added pyridine (1.25 g), then cyanomethanesulfonyl chloride (2 g) and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into 50 ml water and the pH was made basic by addition of 1N aqueous sodium hydroxide. The aqueous layer was extracted with ethyl acetate, the combined organic layers were dried over sodium sulfate, then concentrated in vacuo. Column chromatography (ethyl acetate/cyclohexane 1:1) afforded the title product as an orange solid (590 mg). 1HNMR (CDCl3, 400 MHz): 7.30 (d, 2H), 6.95 (d, 2H), 6.70 (m, 1H), 3.95 (s, 2H), 3.85 (s, 3H).

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. dry with materialthe combined organic layers were dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-035b5954c6f84e0b84e1c303b02a24f2
Source dataset
uspto-grants-2014_05
Patent number
US08735362B2

Reaction notes

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