Methyl iodide → HCID 13241366, compound

HRID 1607904Notes

Reaction equation

HRID 1607904 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 hadbeen 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 wasfiltered off with suction, washed with acetone and suspended in methylene chloride, and saturated sodium bicarbonate solution was added. The organicphase 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 hadbeen 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. washwashed with acetone
  12. additionsaturated sodium bicarbonate solution was added
  13. customThe organicphase was separated off
  14. washwashed
  15. concentrationconcentrated

Sources & evidence

ORD record
ord-f154275ddeaa47b9bec4e01bb3583d80
Source dataset
uspto-grants-1989_09
Patent number
US04868196

Reaction notes

Loading…