Cyanuric chloride → 2,4-Dichloro-6-morpholino-1,3,5-triazine

HRID 536874Notes

Reaction equation

HRID 536874 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[N:7]1[C:14]([Cl:15])=[N:13][C:11](Cl)=[N:10][C:8]=1[Cl:9]>C(Cl)(Cl)Cl.O>[Cl:9][C:8]1[N:7]=[C:14]([Cl:15])[N:13]=[C:11]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[N:10]=1

Participants

5

Reactant 2

HCID 7954Cyanuric chlorideHCID 8083Morpholine

Product 1

HCID 810762,4-Dichloro-6-morpholino-1,3,5-triazineYield 39.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
-5 °C

Procedure

Morpholine (9.5 mL, 108 mmol)) was added to a solution of cyanuric chloride (20 g, 108 mmol) in chloroform (10 mL) and stirred at −5° C. for 1 hour. Reaction mixture was diluted with water, extracted with dichloromethane. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Crude product was purified by silica gel (100-200 mesh) column chromatography using 5% ethyl acetate in pet-ether as an eluent to give 4-(4,6-dichloro-1,3,5-triazin-2-yl)morpholine (10 g, 39% yield).

Workup

  1. customReaction mixture
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customCrude product was purified by silica gel (100-200 mesh) column chromatography

Sources & evidence

ORD record
ord-dbee2f893e334c579c5c912c0dd0d396
Source dataset
uspto-grants-2014_10
Patent number
US08859542B2

Reaction notes

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