Iodoethane → HCID 6482603, compound

HRID 426786Notes

Reaction equation

HRID 426786 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[C:12]([CH3:17])=[N:13][NH:14][C:15]=1[CH3:16].[H-].[Na+].[CH2:26](I)[CH3:27]>CN(C)C=O>[Cl:1][C:2]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[C:15]([CH3:16])=[N:14][N:13]([CH2:26][CH3:27])[C:12]=1[CH3:17]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 6482601HCID 6482601, compound

Product 1

HCID 6482603HCID 6482603, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6.8 g of 4-[6-(2-chloro-4-methoxyphenoxy)hexyl]-3,5-dimethyl-1H-pyrazole (Example 7) in 100 ml of dimethylformamide was added 1.13 g of sodium hydride. The mixture was stirred one hour at room temperature, and then 3.8 g of ethyl iodide was added and the reaction mixture stirred for six hours longer. The reaction mixture was concentrated to remove the solvent, the residue partitioned between dilute hydrochloric acid and methylene dichloride, and the organic layer washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was chromatographed on silica with hexane:ethyl acetate:acetonitrile 4:2:1 to give 2.6 g of 4-[6-(2-chloro-4-methoxyphenoxy)hexyl]-1-ethyl-3,5-dimethyl-1H-pyrazole as a pale yellow oil; MIC=0.7-1.5 microg/ml (herpes 1 and 2).

Workup

  1. stirringthe reaction mixture stirred for six hours longer
  2. concentrationThe reaction mixture was concentrated
  3. customto remove the solvent
  4. customthe residue partitioned between dilute hydrochloric acid and methylene dichloride
  5. washthe organic layer washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica with hexane:ethyl acetate:acetonitrile 4:2:1

Sources & evidence

ORD record
ord-b1c2028d79fc44cba187687846821fd3
Source dataset
uspto-grants-1979_10
Patent number
US04171365

Reaction notes

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