Ammonia → 3-Pyridinesulfonamide, 2-amino-5-bromo-

HRID 241063Notes

Reaction equation

HRID 241063 reaction equation
[NH2:1][C:2]1[C:7]([S:8](Cl)(=[O:10])=[O:9])=[CH:6][C:5]([Br:12])=[CH:4][N:3]=1.[NH3:13]>O1CCOCC1>[NH2:1][C:2]1[C:7]([S:8]([NH2:13])(=[O:10])=[O:9])=[CH:6][C:5]([Br:12])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 533020262-Amino-5-bromopyridine-3-sulfonyl chloride

Product 1

HCID 523351763-Pyridinesulfonamide, 2-amino-5-bromo-Yield 89%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Amino-5-bromopyridine-3-sulfonyl chloride (reagent preparation 25) (95.5 mg, 0.35 mmol) was treated with 0.5M ammonia in dioxane solution (7 mL) and the mixture was stirred for 1 h at room temperature. Concentrated aqueous ammonia (2 mL) was then added to the mixture then stirred an additional 12 h. The mixture was then concentrated and the residue suspended in water (5 mL). The solid was collected by filtration and dried to give 2-amino-5-bromopyridine-3-sulfonamide (55.7 mg, 89%).

Workup

  1. stirringthen stirred an additional 12 h
  2. concentrationThe mixture was then concentrated
  3. filtrationThe solid was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-e5320d8f4f554ff1ad962cc3902c6112
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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