1H-1,2,4-Triazole → 2-(1-Imidazolyl)-4-dimethylamino-6-(1H-1,2,4-triazole-1-yl)-1,3,5-triazine

HRID 2395618Notes

Reaction equation

HRID 2395618 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)[N:5]=[C:4]([N:13]([CH3:15])[CH3:14])[N:3]=1.[NH:16]1[CH:20]=[N:19][CH:18]=[N:17]1>CN(C=O)C>[N:8]1([C:6]2[N:5]=[C:4]([N:13]([CH3:15])[CH3:14])[N:3]=[C:2]([N:16]3[CH:20]=[N:19][CH:18]=[N:17]3)[N:7]=2)[CH:12]=[CH:11][N:10]=[CH:9]1

Participants

4

Reactant 2

HCID 92571H-1,2,4-TriazoleHCID 105133592-Chloro-4-(1-imidazolyl)-6-dimethylamino-1,3,5-triazine

Product 1

HCID 189894262-(1-Imidazolyl)-4-dimethylamino-6-(1H-1,2,4-triazole-1-yl)-1,3,5-triazineYield 17.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The obtained 2-chloro-4-(1-imidazolyl)-6-dimethylamino-1,3,5-triazine (113 mg, 0.503 mmol) was dissolved in DMF (1 ml), added with 1,2,4-triazole (149 mg, 2.15 mmol) and stirred at 110° C.-120° C. for 4 hours. The reaction mixture was evaporated under reduced pressure. The obtained 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 solvent was removed under reduced pressure and the obtained residue was purified by silica gel column chromatography, using ethyl acetate and methanol (9:1) as eluant, to obtain 22.7 mg (yield: 17.6%) of the titled compound as colorless crystals.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. additionThe obtained 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 solvent was removed under reduced pressure
  9. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f307fb1ca9744d36b0de154863fdc200
Source dataset
uspto-grants-1996_02
Patent number
US05489591

Reaction notes

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