Sodium Iodide → HCID 57861963, compound

HRID 1095427Notes

Reaction equation

HRID 1095427 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:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20]Br.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O>[Br:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:14][C:11]1[CH:12]=[CH:13][N:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[N:10]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 21521Bis(2-bromoethyl) etherHCID 178516421HCID 178516421, compound

Product 1

HCID 57861963HCID 57861963, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(3,4-dichlorophenyl)-1H-pyrazol-3-ol (229 mg, 1 mmol; compound prepared in the same way as Example 1, Scheme 1-step 1B), 1-bromo-2-(2-bromoethoxy)ethane (515 mg, 2 mmol), potassium carbonate (0.42 g, 3 mmol) and sodium iodide (0.15 g, 1 mmol) in dimethylformamide (12 ml) was stirred, under dry nitrogen atmosphere, at room temperature overnight. The inorganic solid was filtered off and solvent was evaporated to dryness in vacuo. The remaining residue was 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, 466 mg of 3-(2-(2-bromoethoxy)ethoxy)-1-(3,4-dichlorophenyl)-1H-pyrazole which was used without further purification in the next step of synthesis.

Workup

  1. filtrationThe inorganic solid was filtered off
  2. customsolvent was evaporated to dryness in vacuo
  3. customThe remaining residue was partitioned 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. custom466 mg of 3-(2-(2-bromoethoxy)ethoxy)-1-(3,4-dichlorophenyl)-1H-pyrazole which was used without further purification in the next step of synthesis

Sources & evidence

ORD record
ord-d55b4166fdeb48718602880d8b167b1a
Source dataset
uspto-grants-2012_03
Patent number
US08138186B2

Reaction notes

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