Pyridine → HCID 54291171, compound

HRID 1065022Notes

Reaction equation

HRID 1065022 reaction equation
[N:1]1C=CC=[N:3][C:2]=1[CH2:7][NH:8][C:9]1[C:14](C)=[CH:13][CH:12]=[CH:11][C:10]=1C.N1C=CC=C[CH:18]=1.[Cl:23][CH2:24][C:25](Cl)=[O:26].O1[CH2:32][CH2:31][CH2:30][CH2:29]1>>[CH3:18][CH:24]([Cl:23])[C:25]([N:8]([CH2:7][C:2]1[N:1]=[CH:32][CH:31]=[C:30]([CH3:29])[N:3]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:26]

Participants

5

Reactant 4

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 8028TetrahydrofuranHCID 12877376HCID 12877376, compound

Product 1

HCID 54291171HCID 54291171, compoundYield 71%

Procedure

8.5 g (0.04 mol) of N-(pyrimidin-2-yl-methyl)-2,6-dimethylaniline and 3.2 g (0.04 mol) of pyridine were heated under reflux in 20 ml of tetrahydrofuran. 4.5 g (0.04 mol) of chloroacetyl chloride were added dropwise to this mixture. The reaction mixture was stirred under reflux for 5 hours and then poured onto 300 g of ice. The crystalline precipitate formed was filtered off, washed with water and recrystallized from carbon tetrachloride. 8.2 g (71% of theory) of 2,6-dimethyl-N-(pyrimidin-2-yl-methyl)-chloroacetanilide were obtained in the form of colorless crystals of melting point 110° C.

Workup

  1. temperatureunder reflux for 5 hours
  2. customThe crystalline precipitate formed
  3. filtrationwas filtered off
  4. washwashed with water
  5. customrecrystallized from carbon tetrachloride

Sources & evidence

ORD record
ord-94896d8e14834d26b9b6b5bf0df44c80
Source dataset
uspto-grants-1982_05
Patent number
US04328029

Reaction notes

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