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2-Methoxyethylamine → N-(2-methoxyethyl)methanesulfonamide

HRID 1776171
Notes
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Reaction equation

HRID 1776171 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].C(N(CC)C(C)C)(C)C.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][NH:5][S:16]([CH3:15])(=[O:18])=[O:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 80182-MethoxyethylamineHCID 31297Methanesulfonyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 3522477N-(2-methoxyethyl)methanesulfonamideYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-methoxyethylamine (2.67 mL, 31.0 mmol) in anhydrous methylene chloride (100 mL) and N,N-diisopropylethyl amine (8.54 mL, 51.7 mmol) at 0° C. was slowly added methanesulfonyl chloride (2.0 mL, 25.8 mmol). The reaction mixture was slowly warmed to room temperature and stirred overnight. The mixture was concentrated and the residue was purified by silica gel column chromatography (0-100% ethyl acetate in hexanes) to afford the product as a colorless oil (2.8 g, 71%). 1H NMR (300 MHz, CDCl3) δ 4.66 (br s, 1H), 3.54 (t, 2H, J=4.8 Hz), 3.39 (s, 3H), 6.37-3.29 (m, 2H), 3.00 (s, 3H).

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes

Workup

  1. customat 0° C.
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by silica gel column chromatography (0-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-f97df20e9feb43f0860b963d98de82da
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09265772B2

Reaction notes

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