Pyridine → Methanesulfonamide, N-phenyl-

HRID 65237

Reaction equation

HRID 65237 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:14][S:15](Cl)(=[O:17])=[O:16]>C(Cl)Cl>[C:2]1([NH:1][S:15]([CH3:14])(=[O:17])=[O:16])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6115AnilineHCID 31297Methanesulfonyl chloride

Product 1

HCID 70970Methanesulfonamide, N-phenyl-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 250 g (2.68 mole) of aniline and 233.2 g (2.95 mole) of pyridine in 1.25 L of methylene chloride and 319.6 g (2.79 mole) of methanesulfonyl chloride dropwise. Stir the resulting solution at 0° C. for about 30 minutes then warm to ambient temperature for about 16 hours. Extract the mixture with 2N aqueous sodium hydroxide (4×1 L). Combine the aqueous extracts and wash with 1 L of methylene chloride. Cool the aqueous layer to about 0° C. and acidify with concentrated hydrochloric acid until about pH 1. Collect the precipitate and dry to give the title compound.

Workup

  1. customTo a 0° C.
  2. temperaturethen warm to ambient temperature for about 16 hours
  3. extractionExtract the mixture with 2N aqueous sodium hydroxide (4×1 L)
  4. washCombine the aqueous extracts and wash with 1 L of methylene chloride
  5. temperatureCool the aqueous layer to about 0° C.
  6. customCollect the precipitate
  7. customdry

Sources & evidence

ORD record
ord-fb68f984a46c4939bbfa1222749812bc
Source dataset
uspto-grants-1986_09
Patent number
US04613609

Linked notes

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