Morpholine → 2-chloro-4-(N-methyl-N-phenylamino)-6-morpholino-1,3,5-triazine

HRID 2395614Notes

Reaction equation

HRID 2395614 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([N:9]([CH3:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>CN(C=O)C>[Cl:8][C:6]1[N:5]=[C:4]([N:9]([CH3:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:3]=[C:2]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[N:7]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 198964,6-dichloro-N-methyl-N-phenyl-1,3,5-triazin-2-amine

Product 1

HCID 108284402-chloro-4-(N-methyl-N-phenylamino)-6-morpholino-1,3,5-triazineYield 83.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The obtained 2,4-dichloro-6-(N-methyl-N-phenylamino)-1,3,5-triazine (956 mg, 3.75mmol) was dissolved in DMF (10 ml), added with anhydrous potassium carbonate (518 mg, 3.77 mmol), cooled to -5° C.-0° C. and gradually added dropwise with morpholine (359 mg, 4.13 mmol) dissolved in DMF (5 ml). The reaction mixture was stirred at room temperature for 24 hours and evaporated under reduced pressure. The residue was added with ethyl acetate and 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 (20:1) as eluant, to obtain 958 mg (yield: 83.5%) of 2-chloro-4-(N-methyl-N-phenylamino)-6-morpholino-1,3,5-triazine as colorless crystals having melting point of 93.5° C.-95.5° C.

Workup

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

Sources & evidence

ORD record
ord-ea17c9f8c78a441eb3b29b07e252f28c
Source dataset
uspto-grants-1996_02
Patent number
US05489591

Reaction notes

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