Pyridine → Sulfanilamide

HRID 2235820Notes

Reaction equation

HRID 2235820 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[S:9](Cl)(=[O:11])=[O:10].[N:13]1C=CC=CC=1>C(Cl)Cl>[CH:7]1[C:2]([NH2:1])=[CH:3][CH:4]=[C:5]([S:9]([NH2:13])(=[O:11])=[O:10])[CH:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6115AnilineHCID 31297Methanesulfonyl chloride

Product 1

HCID 5333Sulfanilamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 0° C. solution of the aniline from step E (940 mg, 4.0 mmol) in 30 mL of DCM and 5 mL of pyridine was added methanesulfonyl chloride (0.40 mL, 4.0 mmol). The resulting mixture was stirred at this temperature for 2 h before being diluted with 100 mL of DCM. The solution was washed with 1N HCl (3×25 mL), water (2×25 mL), and brine (25 mL). The organic phase was dried and concentrated to afford sulfonamide P which was used in the next step without further purification. LCMS (M+H)=314.1

Workup

  1. washThe solution was washed with 1N HCl (3×25 mL), water (2×25 mL), and brine (25 mL)
  2. customThe organic phase was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e88d8b023ed346ccb3790ec5667c8a49
Source dataset
uspto-grants-2010_05
Patent number
US07714021B2

Reaction notes

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