Diethyl Ether → N-amino-2-(1-butynyl)pyridinium mesitylenesulfonate

HRID 1864981Notes

Reaction equation

HRID 1864981 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1)#[C:2][CH2:3][CH3:4].[C:11]1([CH3:24])[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[C:12]=1[S:19]([O:22][NH2:23])(=[O:21])=[O:20].C(OCC)C>ClCCl>[C:11]1([CH3:24])[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[C:12]=1[S:19]([O-:22])(=[O:21])=[O:20].[NH2:23][N+:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:1]#[C:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamineHCID 212993912-(1-Butynyl)pyridine

Product 1

HCID 21984654N-amino-2-(1-butynyl)pyridinium mesitylenesulfonateYield 39.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

After dissolving 2-(1-butynyl)pyridine (12.8 g) in dichloromethane (60 mL), a solution of O-mesitylenesulfonylhydroxyamine (Reference document: Synthesis, 1997, 1) (20 g) in dichloromethane (132 mL) was added dropwise while cooling on ice, and the mixture was stirred for 30 minutes. Diethyl ether (2 L) was added to the reaction mixture to precipitate crystals, which were collected by filtration and dried under reduced pressure to obtain N-amino-2-(1-butynyl)pyridinium mesitylenesulfonate (12.6 g) as colorless crystals.

Workup

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

Sources & evidence

ORD record
ord-fb682ec0c8fb4eed88f783a154d21b64
Source dataset
uspto-grants-2009_12
Patent number
US07625925B2

Reaction notes

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