Pyridine → N-(2,6-dimethyl-3-pyridyl)-alpha-chloroacetamide

HRID 1973232

Reaction equation

HRID 1973232 reaction equation
[CH3:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.N1C=CC=CC=1.[Cl:16][CH2:17][C:18](Cl)=[O:19]>CCOCC>[CH3:1][C:2]1[C:7]([NH:8][C:18](=[O:19])[CH2:17][Cl:16])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 769642,6-Dimethyl-3-pyridylamine

Product 1

HCID 21493317N-(2,6-dimethyl-3-pyridyl)-alpha-chloroacetamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 2,6-dimethyl-3-aminopyridine (24.9 grams) in ether (200 ml), and pyridine (21 grams) are charged into a glass reaction vessel equipped with mechanical stirrer, thermometer and addition funnel. The reaction mixture is cooled to a temperature below about 10° C and chloroacetyl chloride (11.3 grams) is slowly added over a period of about 15 minutes. Stirring and cooling is continued for an additional period of about 1 hour to ensure the completion of the reaction. The resulting precipitate is then recovered by filtration, is washed with aqueous potassium carbonate and with water, and is dried to yield the desired product N-(2,6-dimethyl-3-pyridyl)-α-chloroacetamide.

Workup

  1. customequipped with mechanical stirrer
  2. additionthermometer and addition funnel
  3. additionis slowly added over a period of about 15 minutes
  4. temperaturecooling
  5. customthe completion of the reaction
  6. filtrationThe resulting precipitate is then recovered by filtration
  7. washis washed with aqueous potassium carbonate and with water
  8. customis dried

Sources & evidence

ORD record
ord-da0b738a75b04e429fcb47a862999556
Source dataset
uspto-grants-1976_12
Patent number
US03996352

Linked notes

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