Calcium Chloride → 1-Methyl-5-[[(1-propylimidazol-5-yl)methyl]thio]-1,2,4-triazole-3-amine

HRID 856736Notes

Reaction equation

HRID 856736 reaction equation
[CH3:1][N:2]1[C:6]([S:7][CH2:8][C:9]2[N:13]([CH2:14][CH2:15][CH3:16])[CH:12]=[N:11][CH:10]=2)=[N:5][C:4]([N+:17]([O-])=O)=[N:3]1.[Cl-].[Ca+2].[Cl-]>C(O)C>[CH3:1][N:2]1[C:6]([S:7][CH2:8][C:9]2[N:13]([CH2:14][CH2:15][CH3:16])[CH:12]=[N:11][CH:10]=2)=[N:5][C:4]([NH2:17])=[N:3]1

Participants

4

Reactant 2

HCID 5284359Calcium ChlorideHCID 695218171-Methyl-3-nitro-5-[[(1-propylimidazol-5-yl)methyl]thio]-1,2,4-triazole

Product 1

HCID 695227661-Methyl-5-[[(1-propylimidazol-5-yl)methyl]thio]-1,2,4-triazole-3-amineYield 34.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 1-methyl-3-nitro-5-[[(1-propylimidazol-5-yl)methyl]thio]-1,2,4-triazole (2.8 g) was added 85% ethanol solution (84 ml), calcium chloride (0.57 g) and reduced iron (2.9 g) were added to the mixture, and the mixture was heated to reflux for 3 hours. After cooling to room temperature, the mixture was filtered with Celite, and washed with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 1-methyl-5-[[(1-propylimidazol-5-yl)methyl]thio]-1,2,4-triazole-3-amine (0.86 g).

Workup

  1. additionwere added to the mixture
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 3 hours
  4. filtrationthe mixture was filtered with Celite
  5. washwashed with ethyl acetate
  6. washThe organic layer was washed with water and saturated brine
  7. dry with materialdried over 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-e5300d27c77243a098bfbefebabc6c58
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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