Cyanuric chloride → HCID 118413341, compound

HRID 1773850Notes

Reaction equation

HRID 1773850 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.C([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])C>C(#N)C>[CH2:20]([N:17]([CH2:18][CH3:19])[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)[CH3:21]

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 8471TriethylamineHCID 67180Acetone, oxime

Product 1

HCID 118413341HCID 118413341, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of acetone oxime (4.68 g, 0.063 mol) and cyanuric chloride (3.69 g, 0.020 mol) in dry acetonitrile (40 ml) is at room temperature added triethylamine (6.38 g, 0.063 mol). The temperature of the reaction mixture at the end of the addition rises up to 44° C. The mixture is then stirred for 21 h at 45° C., cooled to 8° C., the precipitated solid is filtered off and the filtrate is evaporated under reduced pressure. The residue is washed thoroughly with water and dried to afford 2.96 g of the title compound as a white solid, mp. 111-113° C.

Workup

  1. customis at room temperature
  2. additionThe temperature of the reaction mixture at the end of the addition
  3. customrises up to 44° C
  4. temperaturecooled to 8° C.
  5. filtrationthe precipitated solid is filtered off
  6. customthe filtrate is evaporated under reduced pressure
  7. washThe residue is washed thoroughly with water
  8. customdried

Sources & evidence

ORD record
ord-1e2ad89641a24288a780ec1a4b3155a5
Source dataset
uspto-grants-2016_02
Patent number
US09255217B2

Reaction notes

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