Cyanuric chloride → HCID 87242098, compound

HRID 1773848Notes

Reaction equation

HRID 1773848 reaction equation
[C:1]1(=[N:13][OH:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:15]1[C:22](Cl)=[N:21][C:19](Cl)=[N:18][C:16]=1Cl>N1C=CC=CC=1>[C:1]1(=[N:13][O:14][C:16]2[N:18]=[C:19]([O:14][N:13]=[C:1]3[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[N:21]=[C:22]([O:14][N:13]=[C:1]3[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[N:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 7954Cyanuric chlorideHCID 136762Cyclododecanone, oxime

Product 1

HCID 87242098HCID 87242098, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a cold (0° C.) solution of cyclododecanone oxime (7.89 g, 0.04 mol) in dry pyridine (30 ml) is added cyanuric chloride (1.84 g, 0.01 mol). An exothermic reaction occurs and the temperature rises to 20° C. The solution is then stirred 20 h at room temperature and then poured into 300 ml of ice-cold water. The precipitated solid is filtered off and chromatographed (silica gel, CH2Cl2—C2H5O(CO)CH3 95:5). The pure fraction is recrystallized from ethylacetate-hexane to afford 2.36 g of the title compound as a white solid, m.p. 104-107° C.

Workup

  1. customAn exothermic reaction
  2. customrises to 20° C
  3. filtrationThe precipitated solid is filtered off
  4. customchromatographed (silica gel, CH2Cl2—C2H5O(CO)CH3 95:5)
  5. customThe pure fraction is recrystallized from ethylacetate-hexane

Sources & evidence

ORD record
ord-39f6a780cc9a4685bd2f03a7c5688c27
Source dataset
uspto-grants-2016_02
Patent number
US09255217B2

Reaction notes

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