Sodium Iodide → HCID 57861967, compound

HRID 1095425Notes

Reaction equation

HRID 1095425 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[CH:12][C:11]([OH:14])=[N:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].Br[CH2:16][CH2:17][OH:18].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][CH2:16][CH2:17][OH:18])=[N:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 178516421HCID 178516421, compound

Product 1

HCID 57861967HCID 57861967, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-(3,4-dichlorophenyl)-1H-pyrazol-3-ol (238 mg, 1.04 mmol; compound prepared in the same way as Example 1, Scheme 1-step 1B), 2-bromoethanol (273 mg, 2.08 mmol), potassium carbonate (0.43 g, 3.12 mmol) and sodium iodide (0.16 g, 1.04 mmol) in dimethylformamide (5 ml) was warmed, under dry nitrogen atmosphere, with stirring, to 60° C. overnight. The solvent was evaporated to dryness in vacuo and residue partitioned between water and ethyl ether. The combined organic phases were washed with water and dried over sodium sulphate, filtered and evaporated in vacuo. The residue was stirred with petroleum ether at 45° C. and decanted for 3 times to yield, after drying, 258 mg of 2-(1-(3,4-dichlorophenyl)-1H-pyrazol-3-yloxy)ethanol which was used without further purification in the next step of synthesis

Workup

  1. temperaturewas warmed, under dry nitrogen atmosphere
  2. customThe solvent was evaporated to dryness in vacuo and residue
  3. custompartitioned between water and ethyl ether
  4. washThe combined organic phases were washed with water
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. stirringThe residue was stirred with petroleum ether at 45° C.
  9. customdecanted for 3 times
  10. customto yield
  11. customafter drying
  12. custom258 mg of 2-(1-(3,4-dichlorophenyl)-1H-pyrazol-3-yloxy)ethanol which was used without further purification in the next step of synthesis

Sources & evidence

ORD record
ord-35a8c0e28261433694f8d9ecea587767
Source dataset
uspto-grants-2012_03
Patent number
US08138186B2

Reaction notes

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