2-Methoxyethylamine → N-(2-methoxyethyl)-1-phenylmethanesulfonamide

HRID 2421946Notes

Reaction equation

HRID 2421946 reaction equation
[C:1]1([CH2:7][S:8](Cl)(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:12][O:13][CH2:14][CH2:15][NH2:16]>C1COCC1>[CH3:12][O:13][CH2:14][CH2:15][NH:16][S:8]([CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 74740Phenylmethanesulfonyl chloride

Product 1

HCID 4467329N-(2-methoxyethyl)-1-phenylmethanesulfonamideYield 99.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Phenylmethanesulfonyl chloride (3.0 g, 15.7 mmol) was dissolved in dry THF (15 mL) and it was added dropwise to a solution of 2-methoxyethylamine (2.36 g, 31.5 mmol) in dry THF (50 mL) at 0° C. After addition the ice-bath was removed and the reaction was stirred at rt for 2.5 h. The solvent was removed in vacuo and the residue was dissolved in DCM. The mixture was washed with one portion of 5% aqueous HCl, several portions of water, dried through a phase separator and evaporated to give the title compound (3.58 g, 94%); 1H NMR (400 MHz, CDCl3): δ 7.43-7.35 (m, 5H), 4.52 (br s, 1H), 4.26 (s, 2H), 3.40 (t, 2H), 3.32 (s, 3H), 3.14-3.09 (m, 2H); Mass Spectrum: M−H+ 228.

Workup

  1. customwas removed
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in DCM
  4. washThe mixture was washed with one portion of 5% aqueous HCl, several portions of water
  5. customdried through a phase separator
  6. customevaporated

Sources & evidence

ORD record
ord-37e519ae18ea46a6ab660c464f9721ca
Source dataset
uspto-grants-2011_06
Patent number
US07960380B2

Reaction notes

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