1-Bromo-3-chloropropane → 5-(5-[(3-chloropropyl)thio]-4-methyl-4H-1,2,4-triazol-3-yl)-2-methylquinoline

HRID 1668555Notes

Reaction equation

HRID 1668555 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[CH:9]=[CH:10][C:11]([CH3:17])=[N:12]3)=[N:5][NH:4][C:3]1=[S:18].Br[CH2:20][CH2:21][CH2:22][Cl:23].[H-].[Na+]>C(O)C>[Cl:23][CH2:22][CH2:21][CH2:20][S:18][C:3]1[N:2]([CH3:1])[C:6]([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[CH:9]=[CH:10][C:11]([CH3:17])=[N:12]3)=[N:5][N:4]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 446275704-methyl-5-(2-methyl-5-quinolinyl)-4H-1,2,4-triazole-3-thiol

Product 1

HCID 251050505-(5-[(3-chloropropyl)thio]-4-methyl-4H-1,2,4-triazol-3-yl)-2-methylquinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 4-methyl-5-(2-methyl-5-quinolinyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (3.6 g, preparation reported in WO 02/40471) in ethanol (60 ml) containing 1-bromo-3-chloropropane (2.0 ml) was carefully added with stirring sodium hydride (0.60 g, 60% in mineral oil). The mixture was heated at reflux for 45 min. Volatiles were evaporated under reduced pressure and the residue submitted to column chromatography (EtOAc—acetone gradient). The material thus obtained was precipitated from hot EtOAc (20 ml) by adding petroleum ether (40-60, 50 ml), cooled and collected by filtration to provide the title compound as colourless crystals (2.1 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 45 min
  3. customVolatiles were evaporated under reduced pressure
  4. customThe material thus obtained
  5. customwas precipitated from hot EtOAc (20 ml)
  6. additionby adding petroleum ether (40-60, 50 ml)
  7. temperaturecooled
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-531ceffb4b454714ae748733115b4c19
Source dataset
uspto-grants-2011_08
Patent number
US07989444B2

Reaction notes

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