2-Butanone oxime → HCID 131734713, compound

HRID 1773846Notes

Reaction equation

HRID 1773846 reaction equation
[CH2:1]([C:3]([CH3:6])=[N:4][OH:5])[CH3:2].[N:7]1[C:14](Cl)=[N:13][C:11](Cl)=[N:10][C:8]=1Cl>N1C=CC=CC=1>[CH3:6]/[C:3](=[N:4]\[O:5][C:8]1[N:10]=[C:11]([O:5]/[N:4]=[C:3](/[CH3:6])\[CH2:1][CH3:2])[N:13]=[C:14]([O:5][N:4]=[C:3]([CH2:1][CH3:2])[CH3:6])[N:7]=1)/[CH2:1][CH3:2]

Participants

4

Reactant 2

HCID 72922-Butanone oximeHCID 7954Cyanuric chloride

Product 1

HCID 131734713HCID 131734713, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a cold (0° C.) solution of ethylmethyl-ketoxime (4.18 g, 0.048 mol) in dry pyridine (16 ml) is added cyanuric chloride (2.21 g, 0.012 mol). An exothermic reaction occurs and the temperature rises to 16° C. The solution is then stirred 12 h at room temperature and then poured into 150 ml of ice-cold water. The resulting emulsion is extracted with dichloromethane (3×30 ml), the extracts are dried over MgSO4 and the solvent is evaporated. The residue is chromatographed (silica gel, CH2Cl2—C2H5O(CO)CH3 8:3) to afford 3.72 g of the title compound as a colorless oil which slowly solidifies on standing, mp. 51-56° C.

Workup

  1. customAn exothermic reaction
  2. customrises to 16° C
  3. extractionThe resulting emulsion is extracted with dichloromethane (3×30 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 8:3)

Sources & evidence

ORD record
ord-cfa2bd03dec84886ac36f00167a8120d
Source dataset
uspto-grants-2016_02
Patent number
US09255217B2

Reaction notes

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