Cyanuric chloride → 2-Chloro-4,6-bis(morpholin-4-yl)-1,3,5-triazine

HRID 2395619Notes

Reaction equation

HRID 2395619 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1>COCCOC>[Cl:3][C:2]1[N:1]=[C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[N:7]=[C:5]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[N:4]=1

Participants

4

Reactant 2

HCID 7954Cyanuric chlorideHCID 8083Morpholine

Product 1

HCID 2249672-Chloro-4,6-bis(morpholin-4-yl)-1,3,5-triazineYield 91.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

Cyanuric chloride (3.63 g, 19.7 mmol) was dissolved in ethylene glycol dimethyl ether (50 ml), cooled to -10° C.-0° C. and gradually added dropwise with morpholine (7.00 ml, 80.3 mmol) dissolved in ethylene glycol dimethyl ether (27 ml). This reaction mixture was stirred at the same temperature for 30 minutes and then stirred at room temperature overnight. The reaction mixture was evaporated under reduced pressure. The residue was added with dichloromethane and water, and then shaken for mixing. The organic layer was separated from the mixture, washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the obtained residue was purified by silica gel column chromatography, using dichloromethane and ethyl acetate (8:2) as eluant, to obtain 5.13 g (yield: 91.2%) of 2-chloro-4,6-dimorpholino-1,3,5-triazine as colorless crystals having melting point of 173.5° C.-174° C.

Workup

  1. temperaturecooled to -10° C.-0° C.
  2. stirringstirred at room temperature overnight
  3. customThe reaction mixture was evaporated under reduced pressure
  4. additionThe residue was added with dichloromethane and water
  5. stirringshaken
  6. additionfor mixing
  7. customThe organic layer was separated from the mixture
  8. washwashed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solvent was removed under reduced pressure
  11. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-edcae99ec2cd4ecabf42ccd0e5d6d006
Source dataset
uspto-grants-1996_02
Patent number
US05489591

Reaction notes

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