Ammonia → pyridine-3-sulfonamide

HRID 1914707Notes

Reaction equation

HRID 1914707 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([S:7](Cl)(=[O:9])=[O:8])[CH:2]=1.[NH3:11].O1CCOCC1>C1COCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([S:7]([NH2:11])(=[O:9])=[O:8])[CH:2]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 312751,4-DioxaneHCID 3164136Pyridine-3-sulfonyl chloride

Product 1

HCID 232710pyridine-3-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of pyridine-3-sulphonyl chloride (1 g, 5.6 mmol, 1 eq, commercially available from Davos) in THF (5 mL) is added ammonia in dioxane (23.9 mL, 2 M, 47.9 mmol, 8.5 eq). The resulting suspension is stirred at room temperature for 1 h. The solvent is removed and the residue is taken up in DCM. The organic phase is washed with a saturated aqueous solution of NH4Cl then brine and the DCM is removed under reduced pressure to afford, after drying under vacuum at 40° C., 637 mg (71%) of the title compound as a yellowish powder. 1H NMR (DMSO-d6) δ 9.20-8.90 (m, 1H), 8.85-8.75 (m, 1H), 8.40-8.05 (m, 1H), 7.80-7.40 (m, 3H).

Workup

  1. customThe solvent is removed
  2. washThe organic phase is washed with a saturated aqueous solution of NH4Cl
  3. custombrine and the DCM is removed under reduced pressure
  4. customto afford
  5. customafter drying under vacuum at 40° C.

Sources & evidence

ORD record
ord-0bffefc84c6744249e18eb82dd197993
Source dataset
uspto-grants-2013_12
Patent number
US08614215B2

Reaction notes

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