Methyl iodide → HCID 13241366, compound

HRID 847330Notes

Reaction equation

HRID 847330 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:23]=[CH:22][C:7]([O:8][CH2:9][C:10]([OH:21])([C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:11][N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)=[C:6]([CH3:24])[CH:5]=1.I[CH3:26]>O1CCOCC1>[Cl:3][C:4]1[CH:23]=[CH:22][C:7]([O:8][CH2:9][C:10]([O:21][CH3:26])([C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:11][N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)=[C:6]([CH3:24])[CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 12763627HCID 12763627, compound

Product 1

HCID 13241366HCID 13241366, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

27 g (0.9 mol) of 80% strength sodium hydride were introduced in portions into a solution of 290 g (0.86 mol) of 2-(4-chloro-2-methyl-phenoxy-methyl)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-2-butanol in 1,600 ml of absolute dioxane at room temperature. The mixture was subsequently stirred at room temperature for 4 hours, and 141.9 g (1 mol) of iodomethane were then added dropwise. The reaction mixture was stirred at 40° C. for 12 hours and another 10 g (0.33 mol) of 80% strength sodium hydride were then added in portions. After the mixture had been stirred at room temperature for three hours, 57 g (0.4 mol) of iodomethane were added and the reaction mixture was subsequently stirred at room temperature for 72 hours. The suspension was filtered, the filtrate was concentrated, the oily residue was taken up in methylene chloride and the methylene chloride mixture was washed twice with water, dried over sodium sulphate and concentrated. 1,5-Naphthalenedisulphonic acid was added to the residue, in acetone, the salt which precipitated was filtered off with suction, washed with acetone and suspended in methylene chloride, and saturated sodium bicarbonate solution was added. The organic phase was separated off, washed and concentrated. 155 g (54% of theory) of 2-(4-chloro-2-methyl-phenoxymethyl)-3,3-dimethyl-2-methoxy- 1-(1,2,4-triazol-1-yl)butane were obtained as a light yellow oil of refractive index nD20 =1.5390.

Workup

  1. stirringThe reaction mixture was stirred at 40° C. for 12 hours
  2. stirringAfter the mixture had been stirred at room temperature for three hours
  3. stirringthe reaction mixture was subsequently stirred at room temperature for 72 hours
  4. filtrationThe suspension was filtered
  5. concentrationthe filtrate was concentrated
  6. washthe methylene chloride mixture was washed twice with water
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated
  9. addition1,5-Naphthalenedisulphonic acid was added to the residue, in acetone
  10. customthe salt which precipitated
  11. filtrationwas filtered off with suction
  12. washwashed with acetone
  13. additionsaturated sodium bicarbonate solution was added
  14. customThe organic phase was separated off
  15. washwashed
  16. concentrationconcentrated

Sources & evidence

ORD record
ord-5ad9ff847d9d4ddb96b072889f915342
Source dataset
uspto-grants-1992_08
Patent number
US05141553

Reaction notes

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