Cyanuric chloride → Acetone, O,O′,O′′-s-triazine-2,4,6-triyltrioxime

HRID 1773845Notes

Reaction equation

HRID 1773845 reaction equation
[CH3:1][C:2](=[N:4][OH:5])[CH3:3].[N:6]1[C:13](Cl)=[N:12][C:10](Cl)=[N:9][C:7]=1Cl>N1C=CC=CC=1>[C:2](=[N:4][O:5][C:7]1[N:9]=[C:10]([O:5][N:4]=[C:2]([CH3:3])[CH3:1])[N:12]=[C:13]([O:5][N:4]=[C:2]([CH3:3])[CH3:1])[N:6]=1)([CH3:3])[CH3:1]

Participants

4

Reactant 2

HCID 7954Cyanuric chlorideHCID 67180Acetone, oxime

Product 1

HCID 90113126Acetone, O,O′,O′′-s-triazine-2,4,6-triyltrioximeYield 94.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a cold (0° C.) solution of acetone oxime (2.92 g, 0.04 mol) in dry pyridine (15 ml) is added cyanuric chloride (1.84 g, 0.01 mol). An exothermic reaction occurs and the temperature rises to 35° C. The solution is then stirred for 5 h at room temperature and then poured into 100 ml of ice-cold water. The resulting emulsion is extracted with dichloromethane (5×20 ml), the extracts are dried over MgSO4 and the solvent is evaporated. The residue is chromatographed (silica gel, CH2Cl2—C2H5O(CO)CH3 7:3) and the pure fraction is recrystallized from dichloromethane-hexane to afford 2.79 g of the title compound as a white solid, mp. 156-158° C.

Workup

  1. customAn exothermic reaction
  2. customrises to 35° C
  3. extractionThe resulting emulsion is extracted with dichloromethane (5×20 ml)
  4. dry with materialthe extracts are dried over MgSO4
  5. customthe solvent is evaporated
  6. customThe residue is chromatographed (silica gel, CH2Cl2—C2H5O(CO)CH3 7:3)
  7. customthe pure fraction is recrystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-5b9e4cb2188a46e0b3aa9ce06b2bfbd0
Source dataset
uspto-grants-2016_02
Patent number
US09255217B2

Reaction notes

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