Ammonia → 6-chloropyridine-3-sulfonamide

HRID 1360808Notes

Reaction equation

HRID 1360808 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH3:12]>O1CCOCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([NH2:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 27927922-Chloro-5-pyridinesulfonyl chloride

Product 1

HCID 12015126-chloropyridine-3-sulfonamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

6-Chloro-pyridine-3-sulfonyl chloride (5.0 g, 0.024 mol) was dissolved in a 0.5M solution of ammonia in dioxane (125 mL) at −5° C. The mixture was allowed to warm to room temperature and the mixture stirred for 1 hour. The mixture was filtered through celite, washed twice with dioxane and concentrated in vacuo to afford 6-choro-pyridine-3-sulfonic acid amide as an off white solid 4.55 g (98% yield). LC@UV215 nm; Rt 1.05: 100%, m/z (ES+): 193/195 (400 MHz; d6-DMSO) 8.79 (1H, d), 8.21 (1H, dd), 7.75 (1H, d) 7.70 (2H, br S).

Workup

  1. filtrationThe mixture was filtered through celite
  2. washwashed twice with dioxane
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fd1c00041ec84488b9aba89de8395f4e
Source dataset
uspto-grants-2011_02
Patent number
US07879884B2

Reaction notes

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