Trichloroisocyanuric Acid → 5-(Chloromethyl)-2,3-dimethylpyrazine

HRID 19742

Reaction equation

HRID 19742 reaction equation
[Cl:1]N1C(=O)N(Cl)C(=O)N(Cl)C1=O.[CH3:13][C:14]1[N:15]=[C:16]([CH3:21])[C:17]([CH3:20])=[N:18][CH:19]=1>ClC(Cl)C>[Cl:1][CH2:13][C:14]1[N:15]=[C:16]([CH3:21])[C:17]([CH3:20])=[N:18][CH:19]=1

Participants

4

Reactant 2

HCID 6909Trichloroisocyanuric AcidHCID 26808Trimethylpyrazine

Product 1

HCID 552982845-(Chloromethyl)-2,3-dimethylpyrazine

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
20 °C

Procedure

7.6 g (32.74 mmol) of trichloroisocyanuric acid are added, over 1 hour, to a solution, maintained at reflux, of 10 g of trimethylpyrazine (81.85 mmol) in 820 ml of dichloroethane. The reaction mixture is refluxed for 6 hours and then cooled to 20° C., stirred for a further 12 hours and filtered. The filtrate is concentrated under reduced pressure, taken up in 200 ml of ethyl ether, filtered again and then concentrated under reduced pressure. 9.6 g of methyldimethylpyrazine chloride are recovered in the form of a mixture, which is used without further purification in the following step.

Workup

  1. temperaturemaintained
  2. temperatureThe reaction mixture is refluxed for 6 hours
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. filtrationfiltered again
  6. concentrationconcentrated under reduced pressure
  7. custom9.6 g of methyldimethylpyrazine chloride are recovered in the form of a mixture, which
  8. customis used without further purification in the following step

Sources & evidence

ORD record
ord-f1156178cb0a47d3a158b5cf8a0dd4dc
Source dataset
uspto-grants-2010_06
Patent number
US07745467B2

Linked notes

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