Sodium hydride → HCID 9924161, compound

HRID 2114630Notes

Reaction equation

HRID 2114630 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[O:7][C:8]1[C:9]([CH2:15][CH3:16])=[N:10][NH:11][C:12]=1[CH2:13][CH3:14].[CH3:21][O:22][CH2:23][CH2:24]Br.[H][H]>CN(C)C=O>[Cl:3][C:4]1[CH:5]=[C:6]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[O:7][C:8]1[C:12]([CH2:13][CH3:14])=[N:11][N:10]([CH2:24][CH2:23][O:22][CH3:21])[C:9]=1[CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 9878953HCID 9878953, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9924161HCID 9924161, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in oil, 34 mg, 0.850 mmol) was added to a stirred solution of 4-(3,5-dichlorophenoxy)-3,5-diethyl-1H-pyrazole of Example 3 (200 mg, 0.701 mmol) and methoxyethyl bromide (117 mg, 0.850 mmol) in dry N,N-dimethylformamide (2ml) at 0° C. under nitrogen. The mixture was stirred at 0° C. for 45 minutes during which time hydrogen was evolved and the yellow solution turned dark brown. The reaction mixture was quenched by the addition of water (5 ml) and the mixture concentrated under reduced pressure. The residue was dissolved in ethyl acetate (20 ml) and washed with water (10 ml) and brine (10 ml) and then dried over magnesium sulphate, filtered and concentrated under reduced pressure to leave a brown oil. The crude product was purified by flash column chromatography on silica gel eluting with pentane:diethyl ether (80:20, by volume) to provide the title compound (140 mg) as a colourless oil.

Workup

  1. customThe reaction mixture was quenched by the addition of water (5 ml)
  2. concentrationthe mixture concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate (20 ml)
  4. washwashed with water (10 ml) and brine (10 ml)
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto leave a brown oil
  9. customThe crude product was purified by flash column chromatography on silica gel eluting with pentane:diethyl ether (80:20, by volume)

Sources & evidence

ORD record
ord-2301399813364d0ba1a5212f403470d0
Source dataset
uspto-grants-2008_10
Patent number
US07435728B2

Reaction notes

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