Diethyl Ether → 1-Amino-2-(3-methoxy-1-propynyl)pyridinium 2,4,6-trimethyl-1-benzenesulfonate

HRID 2253371Notes

Reaction equation

HRID 2253371 reaction equation
[CH3:1][O:2][CH2:3][C:4]#[C:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1.[C:12]1([CH3:25])[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH3:19])[C:13]=1[S:20]([O:23][NH2:24])(=[O:22])=[O:21].C(OCC)C>ClCCl>[CH3:19][C:14]1[CH:15]=[C:16]([CH3:18])[CH:17]=[C:12]([CH3:25])[C:13]=1[S:20]([O-:23])(=[O:22])=[O:21].[NH2:24][N+:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:5]#[C:4][CH2:3][O:2][CH3:1]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamineHCID 138648462-(3-Methoxyprop-1-YN-1-YL)pyridine

Product 1

HCID 230809481-Amino-2-(3-methoxy-1-propynyl)pyridinium 2,4,6-trimethyl-1-benzenesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(3-methoxy-1-propynyl)pyridine (13.2 g) dissolved in dichloromethane (50 mL) was added a solution of O-mesitylenesulfonylhydroxylamine (Reference; Synthesis, 1997, 1) (21 g) in dichloromethane (80 mL) dropwise while cooling with ice, and the reaction mixture was stirred for 30 minutes. Diethyl ether (1 L) was added to the obtained reaction mixture to precipitate crystals, which were collected by filtration and dried under reduced pressure to afford a crude product of 1-amino-2-(3-methoxy-1-propynyl)pyridinium 2,4,6-trimethyl-1-benzenesulfonate as ecru crystals (27.1 g).

Workup

  1. temperaturewhile cooling with ice
  2. customto precipitate crystals, which
  3. filtrationwere collected by filtration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-aee4daef026f4a79bb12566090f72c42
Source dataset
uspto-grants-2008_01
Patent number
US07323569B2

Reaction notes

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