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

HRID 2239543Notes

Reaction equation

HRID 2239543 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-60be09b87bf34ee68b8021ef90f6750c
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

Loading…