Imidazole → HCID 10637792, compound

HRID 2395622Notes

Reaction equation

HRID 2395622 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1>CN(C=O)C>[N:21]1([C:2]2[N:7]=[C:6]([N:21]3[CH:25]=[CH:24][N:23]=[CH:22]3)[N:5]=[C:4]([N:9]3[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)[N:3]=2)[CH:25]=[CH:24][N:23]=[CH:22]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 810762,4-Dichloro-6-morpholino-1,3,5-triazine

Product 1

HCID 10637792HCID 10637792, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The obtained 2,4-dichloro-6-morpholino-1,3,5-triazine (1.17 g, 4.98 mmol) was dissolved in DMF (30 ml), added with anhydrous potassium carbonate (2.91 g, 21.1 mmol) and imidazole (1.43 g, 21.0 mmol) and stirred at room temperature for 17 hours. The reaction mixture was evaporated under reduced pressure. The residue was added with ethyl acetate 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 obtained residue was purified by silica gel column chromatography, using dichloromethane and methanol (95:5) as eluant, to obtain 483 mg (yield: 32.6%) of the titled compound as colorless crystals.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. additionThe residue was added with ethyl acetate and water
  3. stirringshaken
  4. additionfor mixing
  5. customThe organic layer was separated from the mixture
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-543210b656c7409b8ab1fe68df0a921d
Source dataset
uspto-grants-1996_02
Patent number
US05489591

Reaction notes

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