Iodoethane → HCID 21712126, compound

HRID 650497Notes

Reaction equation

HRID 650497 reaction equation
[F:1][C:2]1[C:3]([C:10]2[C:14]([Cl:15])=[C:13]([O:16][CH:17]([F:19])[F:18])[N:12]([CH3:20])[N:11]=2)=[N:4][C:5]([OH:9])=[C:6]([Cl:8])[CH:7]=1.[OH-].[Na+].[CH2:23](I)[CH3:24].CCCCCC.C(OCC)(=O)C>CS(C)=O>[CH2:23]([N:4]1[C:3]([C:10]2[C:14]([Cl:15])=[C:13]([O:16][CH:17]([F:18])[F:19])[N:12]([CH3:20])[N:11]=2)=[C:2]([F:1])[CH:7]=[C:6]([Cl:8])[C:5]1=[O:9])[CH3:24]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 14798Sodium HydroxideHCID 21226206Ethyl acetate hexaneHCID 178481775HCID 178481775, compound

Product 1

HCID 21712126HCID 21712126, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

1.5 g of 3-(3-fluoro-5-chloro-6-hydroxy-2-pyridyl)-4-chloro-5-difluoromethoxy-1-methyl-[1H]-pyrazole (Example P27) are introduced into 6 ml of dimethyl sulfoxide (DMSO). 2.5 ml of a 2N aqueous sodium hydroxide solution are added thereto. 0.78 g of ethyl iodide in 2 ml of DMSO is then added dropwise, with stirring, and the mixture is further stirred overnight at 70° C. The next day, the reaction mixture is partitioned between dilute hydrochloric acid and diethyl ether. After extraction by shaking, and separation of the phases, the ethereal phase is washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. Finally, the residue is purified over a flash chromatography column (silica gel; elution gradient: n-hexane/ethyl acetate 4/1 to 1/1 (v/v)). 0.54 g of the desired target compound is obtained in the form of a yellow oil having an Rf value of 0.17 on silica gel 60 F254 (eluant: n-hexane/-ethyl acetate 2/1 (v/v)).

Workup

  1. stirringthe mixture is further stirred overnight at 70° C
  2. customThe next day, the reaction mixture is partitioned between dilute hydrochloric acid and diethyl ether
  3. extractionAfter extraction
  4. stirringby shaking
  5. customseparation of the phases
  6. washthe ethereal phase is washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customFinally, the residue is purified over a flash chromatography column (silica gel; elution gradient: n-hexane/ethyl acetate 4/1 to 1/1 (v/v))
  11. custom0.54 g of the desired target compound is obtained in the form of a yellow oil

Sources & evidence

ORD record
ord-94d0a885f20e4f1d9c2f17dc76f952b7
Source dataset
uspto-grants-2001_08
Patent number
US06274536B1

Reaction notes

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