2-Methoxyethylamine → HCID 61695057, compound

HRID 2036792Notes

Reaction equation

HRID 2036792 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[N:6][CH:7]=1.[CH3:12][O:13][CH2:14][CH2:15][NH2:16]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([S:8]([NH:16][CH2:15][CH2:14][O:13][CH3:12])(=[O:10])=[O:9])[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 203244745-Bromopyridine-3-sulfonyl chloride

Product 1

HCID 61695057HCID 61695057, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-bromopyridine-3-sulfonyl chloride (1.5 g, 5.8 mmol)) and 2-methoxyethanamine (1.3 g, 18 mmol) in THF (40 mL) was stirred at room temperature for 16 h. After this time, the resulting reaction mixture was partitioned between saturated aqueous sodium chloride and ethyl acetate. The organic solution was dried and evaporated. The resulting residue was purified by flash column chromatography using ethyl acetate/hexanes to yield 5-bromo-N-(2-methoxyethyl)pyridine-3-sulfonamide (460 mg, 27%). LCMS Method T: Retention time 1.13 min; [M+1]=295, 297.

Workup

  1. customAfter this time, the resulting reaction mixture
  2. customwas partitioned between saturated aqueous sodium chloride and ethyl acetate
  3. customThe organic solution was dried
  4. customevaporated
  5. customThe resulting residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-51353fcce4134c6983c945bd7b3be1bc
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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