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

HRID 9179

Reaction equation

HRID 9179 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-a32947a36a4c48d3857c5a4f444f36ff
Source dataset
uspto-grants-2006_08
Patent number
US07091215B2

Linked notes

Loading…