Ethyl Acetate → HCID 59150509, compound

HRID 1668588Notes

Reaction equation

HRID 1668588 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][CH2:23][Cl:24].[H-].[Na+].C(OCC)(=O)C>CCO>[Cl:24][CH2:23][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

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 813641-Bromo-4-chlorobutaneHCID 446275704-methyl-5-(2-methyl-5-quinolinyl)-4H-1,2,4-triazole-3-thiol

Product 1

HCID 59150509HCID 59150509, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Methyl-5-(2-methyl-5-quinolinyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (400 mg) was reacted with 1-bromo-4-chloro-butane (0.233 ml) and NaH (60%, 69 mg) in absolute EtOH (6.5 ml) at reflux for 45 min. Ethyl acetate was added, the insoluble salts were filtered off and the solvent was evaporated under reduced pressure. The crude was purified on silica gel (eluent: ethyl acetate to ethyl acetate/acetone, 1/1) affording the desired compound as pale yellow solid (430 mg, 79% yield).

Workup

  1. temperatureat reflux for 45 min
  2. filtrationthe insoluble salts were filtered off
  3. customthe solvent was evaporated under reduced pressure
  4. customThe crude was purified on silica gel (eluent: ethyl acetate to ethyl acetate/acetone, 1/1)

Sources & evidence

ORD record
ord-d4e499fc50cb4a8da9aef7d70c2a7594
Source dataset
uspto-grants-2011_08
Patent number
US07989444B2

Reaction notes

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