Potassium Iodide → 1-(4-Methoxy-phenyl)-4-[1,2,3]triazol-1-yl-butan-1-one methanesulfonate

HRID 1182183Notes

Reaction equation

HRID 1182183 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[O:6].CC(O)(CC)C.[NH:21]1[CH:25]=[CH:24][N:23]=[N:22]1.[I-].[K+].[OH-].[Na+].[CH3:30][S:31]([OH:34])(=[O:33])=[O:32]>C(OC(C)C)(C)C.C(OCC)(=O)C>[CH3:30][S:31]([OH:34])(=[O:33])=[O:32].[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([C:5](=[O:6])[CH2:4][CH2:3][CH2:2][N:21]2[CH:25]=[CH:24][N:23]=[N:22]2)=[CH:8][CH:9]=1

Participants

8

Reactant 6

HCID 4875Potassium IodideHCID 6395Methanesulfonic AcidHCID 64052-Methyl-2-butanolHCID 14798Sodium HydroxideHCID 964144-Chloro-4'-methoxybutyrophenoneHCID 178418936HCID 178418936, compound

Product 1

HCID 866078301-(4-Methoxy-phenyl)-4-[1,2,3]triazol-1-yl-butan-1-one methanesulfonate

Reagents, catalysts & solvents 1

HCID 22281796Diisopropylether ethyl acetateSolvent

Procedure

10.6 g (50 mmol) 4-Chloro-1-(4-methoxy-phenyl)-butan-1-one, 20 ml 2-methyl-2-butanol, 5.2 g (75 mmol) 1H-[1,2,3]-triazole, 9.5 g (57 mmol) potassium iodide and 3.0 g (75 mmol) NaOH were stirred at 100° C. for 4 h. After removal of solvents in vacuo, the residue was partitioned between toluene and water. Washing of the toluene phase twice with water, drying over sodium sulphate and evaporation gave an oily residue that was dissolved in 80 ml diisopropyl ether/ethyl acetate (1:2). The solution was kept at 20° C. during the addition of 2.8 ml methanesulfonic acid and stirred at room temperature for 2 h. The formed precipitate was isolated, washed with cold diethyl ether and dried at 40° C. in vacuo to give 1-(4-methoxy-phenyl)-4-[1,2,3]triazol-1-yl-butan-1-one methanesulfonate. Yield: 2.25 g (13%).

Workup

  1. customAfter removal of solvents in vacuo
  2. customthe residue was partitioned between toluene and water
  3. washWashing of the toluene phase twice with water
  4. dry with materialdrying over sodium sulphate and evaporation
  5. customgave an oily residue that
  6. customThe formed precipitate was isolated
  7. washwashed with cold diethyl ether
  8. customdried at 40° C. in vacuo

Sources & evidence

ORD record
ord-453b17ff653e438983191caf386e2e68
Source dataset
uspto-grants-2007_10
Patent number
US07288557B2

Reaction notes

Loading…