Pyridine → 4-(Methanesulfonylamino)benzonitrile

HRID 728810Notes

Reaction equation

HRID 728810 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([NH:1][S:17]([CH3:16])(=[O:19])=[O:18])=[CH:3][CH:4]=1)#[N:7]

Participants

4

Reactant 3

HCID 1049PyridineHCID 133964-AminobenzonitrileHCID 31297Methanesulfonyl chloride

Product 1

HCID 27341994-(Methanesulfonylamino)benzonitrile

Procedure

Dissolve 50.3 g (0.426 mol) 4-aminobenzonitrile in 250 mL CH2Cl2with 36 mL (0.445 mol) pyridine. Chill the solution with an ice/MeOH bath and add 34 mL (0.42 mol) methanesulfonyl chloride dropwise, maintaining the reaction temperature below 0° C. Stir the reaction mixture under N2 for 20 h at ambient temperature. After this time, filter thereaction mixture and extract with 3×250 mL 1 N NaOH. Acidify the aqueous layer with concentrated HCl to pH=7. Filter the precipitate to provide the title compound.

Workup

  1. temperatureChill the solution with an ice/MeOH bath
  2. temperaturemaintaining the reaction temperature below 0° C
  3. filtrationAfter this time, filter
  4. extractionmixture and extract with 3×250 mL 1 N NaOH
  5. filtrationFilter the precipitate

Sources & evidence

ORD record
ord-454fe8aa0ca7489e82ad7e5f9501e3cc
Source dataset
uspto-grants-1991_09
Patent number
US05051423

Reaction notes

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