Ethanolamine → 5-Bromo-N-(2-hydroxyethyl)-3-pyridinesulfonamide

HRID 2390133Notes

Reaction equation

HRID 2390133 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([S:9](Cl)(=[O:11])=[O:10])[CH:6]=[N:7][CH:8]=1.C(N(CC)CC)C.[OH:20][CH2:21][CH2:22][NH2:23]>C(Cl)Cl>[Br:2][C:3]1[CH:4]=[C:5]([S:9]([NH:23][CH2:22][CH2:21][OH:20])(=[O:11])=[O:10])[CH:6]=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 8471TriethylamineHCID 441193365-Bromopyridine-3-sulfonyl chloride--hydrogen chloride (1/1)

Product 1

HCID 617955235-Bromo-N-(2-hydroxyethyl)-3-pyridinesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A cooled (0° C.) solution of 5-bromopyridine-3-sulfonyl chloride hydrochloride (3.00 g, 10.2 mmol) in DCM (50 ml) was slowly treated with triethylamine (4.3 ml) and stirred until a clear solution was obtained. This solution was treated dropwise with 2-hydroxyethylamine (0.68 g, 0.68 mL) and stirred at RT for 16 hours. The reaction mixture was washed successively with water and brine, the organic layer was dried with sodium sulfate and evaporated under reduced pressure. The crude product was purified by column chromatography (silica) eluting with 20% ethyl acetate in petroleum ether, to give the title compound.

Workup

  1. customwas obtained
  2. stirringstirred at RT for 16 hours
  3. washThe reaction mixture was washed successively with water and brine
  4. dry with materialthe organic layer was dried with sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe crude product was purified by column chromatography (silica)
  7. washeluting with 20% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-d6f78e09dae6452aa0b38b7d0d7b938f
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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