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

HRID 2253359Notes

Reaction equation

HRID 2253359 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

To a solution of 2-(1-butynyl)pyridine (12.8 g) dissolved in dichloromethane (60 mL) was added a solution of O-mesitylenesulfonylhydroxylamine (Reference; Synthesis, 1997, 1) (20 g) in dichloromethane (132 mL) while cooling with ice, and the reaction mixture was stirred for 30 minutes. Diethyl ether (2 L) was added to the reaction mixture to precipitate crystals, which were filtered off and then dried under reduced pressure to afford a crude product of N-amino-2-(1-butynyl)pyridinium mesitylenesulfonate (12.6 g) as colorless crystals.

Workup

  1. temperaturewhile cooling with ice
  2. customto precipitate crystals, which
  3. filtrationwere filtered off
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-b6b9e4d186364f868aab1295c4ddf53c
Source dataset
uspto-grants-2008_01
Patent number
US07323569B2

Reaction notes

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