Hydrazine → 2-Amino-5-bromopyridine-3-sulfonohydrazide

HRID 241060Notes

Reaction equation

HRID 241060 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.[NH2:13][NH2:14]>C1COCC1>[NH2:1][C:2]1[C:7]([S:8]([NH:13][NH2:14])(=[O:10])=[O:9])=[CH:6][C:5]([Br:12])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 533020262-Amino-5-bromopyridine-3-sulfonyl chloride

Product 1

HCID 668205072-Amino-5-bromopyridine-3-sulfonohydrazide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Amino-5-bromopyridine-3-sulfonyl chloride (94 mg, 0.35 mmol) was taken into THF (2 mL) followed by addition of anhydrous hydrazine (40 uL, 1.4 mmol) and the mixture was stirred for 10 minutes at room temperature. The mixture was concentrated and dried to give 2-amino-5-bromopyridine-3-sulfonohydrazide as a white solid, which was then taken into ethanol (2 mL) followed by addition of sodium acetate (320 mg, 3.9 mmol) and ethyl iodide (140 uL, 1.75 mmol). The mixture was refluxed for 12 h then cooled to room temperature and concentrated. The residue was partitioned with ethyl acetate and water and the organic phase washed with brine then dried over sodium sulfate, filtered and concentrated to give 5-bromo-3-(ethylsulfonyl)pyridin-2-amine (67 mg, 72%) as a yellow oil. MS (EI) for C7H9N2SO2Br: 265, 267 (MH+).

Workup

  1. concentrationThe mixture was concentrated
  2. customdried

Sources & evidence

ORD record
ord-2312c63da48a44fca465a6e78568d88b
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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