Dimethylformamide → 1-Methyl-3-nitro-5-[[(1-propylimidazol-5-yl)methyl]thio]-1,2,4-triazole

HRID 856735Notes

Reaction equation

HRID 856735 reaction equation
[CH3:1][N:2]1[C:6]([SH:7])=[N:5][C:4]([N+:8]([O-:10])=[O:9])=[N:3]1.CN(C=O)C.C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:24][C:25]1[N:29]([CH2:30][CH2:31][CH3:32])[CH:28]=[N:27][CH:26]=1>O>[CH3:1][N:2]1[C:6]([S:7][CH2:24][C:25]2[N:29]([CH2:30][CH2:31][CH3:32])[CH:28]=[N:27][CH:26]=2)=[N:5][C:4]([N+:8]([O-:10])=[O:9])=[N:3]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 229386165-(chloromethyl)-1-propyl-1H-imidazole hydrochlorideHCID 178481937HCID 178481937, compound

Product 1

HCID 695218171-Methyl-3-nitro-5-[[(1-propylimidazol-5-yl)methyl]thio]-1,2,4-triazoleYield 47.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-methyl-3-nitro-1,2,4-triazol-5-thiol (0.66 g) was dissolved in. DMF (13.2 ml), potassium carbonate (1.7 g) and 5-chloromethyl-1-propylimidazole hydrochloride (1.1 g) were added to the mixture, and the mixture was stirred for 18 hours at room temperature. The reaction solution was added to water and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was washed, to give 1-methyl-3-nitro-5-[[(1-propylimidazol-5-yl)methyl]thio]-1,2,4-triazole (0.55 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. washthe obtained residue was washed

Sources & evidence

ORD record
ord-20a9749023a0430e86b7188bde46692b
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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