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

HRID 1922012Notes

Reaction equation

HRID 1922012 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4](Cl)[N:3]=1.[CH3:10][Mg]Br>C1COCC1>[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 178418573HCID 178418573, compound

Product 1

HCID 160832,4-Dichloro-6-methyl-1,3,5-triazineYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,4,6-trichloro-1,3,5-triazine (20 g, 108 mmol, 1.0 equiv) in THF (8 mL) at −10° C., methylmagnesium bromide (45 ml, 135 mmol, 1.25 equiv) was added dropwise. The reaction mixture was allowed to warm to room temperature and was stirred for 2 h. The mixture was poured onto ice-water and stirred for an additional hour. The product was extracted with ethyl acetate, washed with brine, dried with sodium sulfate, filtered, and concentrated under reduced pressure to afford 14 g of the title compound. The crude product was carried forward in the next step. MS (ES+): m/e 186.1 [M+Na]+.

Workup

  1. additionThe mixture was poured onto ice-water
  2. stirringstirred for an additional hour
  3. extractionThe product was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-66dab82198574a68a5201bbf7f886a7d
Source dataset
uspto-grants-2012_05
Patent number
US08173805B2

Reaction notes

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