Pyridine → 1-(Carbamoylmethyl)pyridinium Chloride

HRID 1182371Notes

Reaction equation

HRID 1182371 reaction equation
[Cl:1][CH2:2][C:3]([NH2:5])=[O:4].[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(#N)C>[Cl-:1].[C:3]([CH2:2][N+:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:4])[NH2:5]

Participants

4

Reactant 2

HCID 1049PyridineHCID 6580Chloroacetamide

Product 1

HCID 27564401-(Carbamoylmethyl)pyridinium ChlorideYield 87.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

50.00 g (524.01 mmol) 2-chloroacetamide were suspended in 100 ml acetonitrile. 41.45 g (524.01 mmol) pyridine were added, and the suspension was heated at 90° C. for 10 hours. The suspension was cooled to 22° C., suction filtered and washed with 100 ml hexane. The product 1-carbamoylmethyl-pyridinium chloride (79.10 g) was obtained as colorless crystals after being recrystallized from ethanol, m.p 205.2° C.

Workup

  1. temperatureThe suspension was cooled to 22° C.
  2. filtrationsuction filtered
  3. washwashed with 100 ml hexane

Sources & evidence

ORD record
ord-0bf33059767542ddbf2760ffa1cbab83
Source dataset
uspto-grants-2007_10
Patent number
US07288658B2

Reaction notes

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