Sodium Iodide → HCID 57861964, compound

HRID 1095423Notes

Reaction equation

HRID 1095423 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].Cl[CH2:16][CH:17]1[CH2:19][O:18]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][CH2:16][CH:17]3[CH2:19][O:18]3)=[N:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 178516421HCID 178516421, compound

Product 1

HCID 57861964HCID 57861964, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(3,4-dichlorophenyl)-1H-pyrazol-3-ol (0.2 g, 0.87 mmol; compound prepared in the same way as Example 1, Scheme 1-step 1B), 2-(chloromethyl)oxirane (0.1 g, 1.05 mmol), potassium carbonate (0.36 g, 2.62 mmol) and sodium iodide (0.13 g, 0.87 mmol) in dimethylformamide (6 ml) was warmed, with stirring, to 100° C. for 4 hrs. The solvent was evaporated to dryness in vacuo and residue partitioned between water and dichlorometane. The combined organic phases were dried over sodium sulphate, filtered and evaporated in vacuo to yield 0.24 g of 1-(3,4-dichlorophenyl)-3-(oxiran-2-ylmethoxy)-1H-pyrazole as a dark oil, used without further purification in next step of synthesis.

Workup

  1. temperaturewas warmed
  2. customThe solvent was evaporated to dryness in vacuo and residue
  3. custompartitioned between water and dichlorometane
  4. dry with materialThe combined organic phases were dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-c9ecc797c0d54661aaeec6ccc4c0750f
Source dataset
uspto-grants-2012_03
Patent number
US08138186B2

Reaction notes

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