Cyanuric chloride → 2,4-Dichloro-6-methyl-1,3,5-triazine

HRID 522918Notes

Reaction equation

HRID 522918 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4](Cl)[N:3]=1.[CH3:10][Mg]Cl>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([CH3:10])[N:3]=1

Participants

4

Reactant 2

HCID 7954Cyanuric chlorideHCID 178418332HCID 178418332, compound

Product 1

HCID 160832,4-Dichloro-6-methyl-1,3,5-triazineYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,4,6-trichloro-1,3,5-triazine (1.0 g, 5.4 mmol) in CH2Cl2 (17 mL) was added MeMgCl (1.8 mL) drop wise and the reaction mixture was stirred at RT for 0.5 h. The reaction mixture was quenched with saturated NH4Cl solution and extracted with EtOAc (2×50 mL). The organic extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 2,4-dichloro-6-methyl-1,3,5-triazine (0.800 g, 90%) as a solid. The crude material was taken to the next step without further purification.

Workup

  1. customThe reaction mixture was quenched with saturated NH4Cl solution
  2. extractionextracted with EtOAc (2×50 mL)
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-96ac45a427d04c538ef267ce2e2e0730
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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