Methyl iodide → 1H-1,2,4-Triazole-1-ethanol, alpha-(1-chlorocyclopropyl)-alpha-((2-chlorophenyl)methyl)-5-(methylthio)-

HRID 481470Notes

Reaction equation

HRID 481470 reaction equation
[Cl:1][C:2]1([C:5]([OH:21])([CH2:14][N:15]2[C:19]([SH:20])=[N:18][CH:17]=[N:16]2)[CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:13])[CH2:4][CH2:3]1.[C:22](=O)([O-])[O-].[K+].[K+].CI.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[Cl:1][C:2]1([C:5]([OH:21])([CH2:14][N:15]2[C:19]([S:20][CH3:22])=[N:18][CH:17]=[N:16]2)[CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:13])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 178520209HCID 178520209, compound

Product 1

HCID 185067551H-1,2,4-Triazole-1-ethanol, alpha-(1-chlorocyclopropyl)-alpha-((2-chlorophenyl)methyl)-5-(methylthio)-Yield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 3.43 g (10 mmol) of 2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-mercapto-1,2,4-triazol-1-yl)-propan-2-ol, 20 ml of absolute acetonitrile and 1.38 g of (10 mmol) of potassium carbonate is treated with 0.93 ml (15 mmol) of methyl iodide and the mixture is stirred at 40° C. for 5 hours. The reaction mixture is then treated with saturated, aqueous sodium carbonate solution and extracted repeatedly using ethyl acetate. The combined organic phases are dried over sodium sulphate and concentrated under reduced pressure. In this manner, 3.4 g (95% of theory) of 2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-methylthio-1,2,4-triazol-1-yl)-propan-2-ol are obtained in the form of oil.

Workup

  1. extractionextracted repeatedly using ethyl acetate
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-faca5f74a0df44b584eea3d993d30686
Source dataset
uspto-grants-1998_08
Patent number
US05789430

Reaction notes

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