Trichloroisocyanuric Acid → HCID 13742925, compound

HRID 2413828Notes

Reaction equation

HRID 2413828 reaction equation
[N:1]1[C:6]([CH3:7])=[CH:5][C:4]([CH3:8])=[CH:3][C:2]=1[CH3:9].[Cl:10]N1C(=O)N(Cl)C(=O)N(Cl)C1=O>C(Cl)(Cl)Cl>[Cl:10][CH2:9][C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[C:6]([CH3:7])[N:1]=1

Participants

4

Reactant 2

HCID 6909Trichloroisocyanuric AcidHCID 79532,4,6-Trimethylpyridine

Product 1

HCID 13742925HCID 13742925, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 121.18 g (1 mole) of 2,4,6-collidine in 400 ml of chloroform was heated at reflux while adding in portions 140 g (0.6 mole) of trichloroisocyanuric acid (min. 90% available chlorine) over 4 hours and stirring was continued for another 30 minutes and then cooled and filtered. The filtrate was admixed with 150 ml of 10% HCl to transform the product into the aqueous phase. The decanted acid aqueous phase was mixed with 150 ml of ethyl acetate and was made alkaline with sodium hydroxide. The decanted aqueous phase was extracted with 100 ml of ethyl acetate. The organic phase was dried and evaporated to dryness under reduced pressure to obtain 45 g (28.9%) of 2-chloromethyl-4,6-dimethyl pyridine with a Cl content of 22.78% (theoretical 22.78%) and a boiling point of 64° to 70° C. at 1 mm Hg.

Workup

  1. temperatureat reflux
  2. temperaturecooled
  3. filtrationfiltered
  4. additionThe decanted acid aqueous phase was mixed with 150 ml of ethyl acetate
  5. extractionThe decanted aqueous phase was extracted with 100 ml of ethyl acetate
  6. customThe organic phase was dried
  7. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-891dfd23be2b4d6c998585b6358d4e59
Source dataset
uspto-grants-1988_01
Patent number
US04719298

Reaction notes

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