Dichloromethane → 1,3,5-Triazin-2-amine, 4-chloro-N,N-dimethyl-6-(4-morpholinyl)-

HRID 2395609Notes

Reaction equation

HRID 2395609 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([N:9]([CH3:11])[CH3:10])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.ClCCl>CN(C=O)C.O>[Cl:8][C:6]1[N:5]=[C:4]([N:9]([CH3:11])[CH3:10])[N:3]=[C:2]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[N:7]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 169852,4-Dichloro-6-(dimethylamino)-1,3,5-triazine

Product 1

HCID 105863421,3,5-Triazin-2-amine, 4-chloro-N,N-dimethyl-6-(4-morpholinyl)-Yield 55.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

The obtained 2,4-dichloro-6-dimethylamino-1,3,5-triazine (1.96 g, 10.2 mmol) was dissolved in DMF (20 ml), added with anhydrous potassium carbonate (1.45 g, 10.5 mmol) and cooled to -5° C.-0° C. This mixture was gradually added dropwise with morpholine (0.96 g, 11.0 mmol) dissolved in DMF (5 ml). The reaction mixture was stirred at room temperature for 17 hours and was evaporated under reduced pressure. The residue obtained was added with dichloromethane and water, and then shaken for mixing. The organic layer was separated from the mixture, sufficiently washed with water, dried over anhydrous magnesium sulfate and evaporated. The residue obtained was purified by silica gel column chromatography, using n-hexane and ethyl acetate (8: 2) as eluant, to obtain 1.37 g (yield: 55.4%) of 2-chloro-4-dimethylamino-6-morpholino-1,3,5-triazine as colorless crystals having melting point of 96° C. -97° C.

Workup

  1. temperaturecooled to -5° C.-0° C
  2. customwas evaporated under reduced pressure
  3. customThe residue obtained
  4. stirringshaken
  5. additionfor mixing
  6. customThe organic layer was separated from the mixture
  7. washsufficiently washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated
  10. customThe residue obtained
  11. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-38db8b9011a24650ae87ce36265d5119
Source dataset
uspto-grants-1996_02
Patent number
US05489591

Reaction notes

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