Sodium Iodide → HCID 24739752, compound

HRID 1095424Notes

Reaction equation

HRID 1095424 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH:16]3[CH2:18][O:17]3)=[N:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH:16]([OH:17])[CH2:18][N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[N:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 57861964HCID 57861964, compound

Product 1

HCID 24739752HCID 24739752, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(3,4-dichlorophenyl)-3-(oxiran-2-ylmethoxy)-1H-pyrazole (0.23 g, 0.82 mmol), morpholine (72 mg, 0.82 mmol), potassium carbonate (0.34 g, 2.47 mmol) and sodium iodide (123 mg, 0.82 mmol) in dimethylformamide (6 ml) was refluxed 8 hrs and the solvent evaporated in vacuo. To the crude residue was added water and dichlorometane, the aqueous solution extracted several times with dichlorometane and the combined organic phases washed with water, dried over sodium sulphate, filtered and evaporated to dryness in vacuo. The crude dark oil obtained, 296 mg, was purified by column chromatography on silica gel (eluent: ethyl acetate/petroleum ether 1:1 to 1:0 and ethyl acetate/CH3OH 9:1) yielding 114 mg of 1-(1-(3,4-dichlorophenyl)-1H-pyrazol-3-yloxy)-3-morpholinopropan-2-ol.

Workup

  1. temperaturewas refluxed 8 hrs
  2. customthe solvent evaporated in vacuo
  3. additionTo the crude residue was added water and dichlorometane
  4. extractionthe aqueous solution extracted several times with dichlorometane
  5. washthe combined organic phases washed with water
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated to dryness in vacuo
  9. customThe crude dark oil obtained
  10. custom296 mg, was purified by column chromatography on silica gel (eluent: ethyl acetate/petroleum ether 1:1 to 1:0 and ethyl acetate/CH3OH 9:1)

Sources & evidence

ORD record
ord-972c415f64774b3b8b1767824d7a5d5e
Source dataset
uspto-grants-2012_03
Patent number
US08138186B2

Reaction notes

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