Thionyl Chloride → HCID 66958824, compound

HRID 1984362Notes

Reaction equation

HRID 1984362 reaction equation
[CH2:1]([N:3]1[C:7]([CH2:8][CH2:9][N:10]2[C:14](=[O:15])[C:13]3=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]3[C:11]2=[O:20])=[CH:6][C:5]([C:21]([NH2:23])=O)=[N:4]1)[CH3:2].S(Cl)(Cl)=O>C1(C)C=CC=CC=1>[CH2:1]([N:3]1[C:7]([CH2:8][CH2:9][N:10]2[C:11](=[O:20])[C:12]3=[CH:19][CH:18]=[CH:17][CH:16]=[C:13]3[C:14]2=[O:15])=[CH:6][C:5]([C:21]#[N:23])=[N:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 66958860HCID 66958860, compound

Product 1

HCID 66958824HCID 66958824, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-ethyl-5-(2-phthalimidoethyl)-1H-pyrazole-3-carboxamide (8.5 g, 27.2 mmol) and thionyl chloride (20 mL) in toluene (40 mL) was heated at reflux for five hours, allowed to cool to ambient temperature, and concentrated under reduced pressure. The residue was dissolved in chloroform and made basic with the addition of 2 M sodium carbonate. The aqueous layer was separated at extracted with chloroform (4×), and the combined organic fractions were washed with brine. The brine was extracted with chloroform (4×). The combined organic fractions were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product (8.08 g) was purified by chromatography on a HORIZON HPFC system (65I cartridge, eluting with chloroform/CMA in a gradient from 100:0 to 80:20) to provide 7.73 g of 1-ethyl-5-(2-phthalimidoethyl)-1H-pyrazole-3-carbonitrile as a white solid.

Workup

  1. temperatureat reflux for five hours
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in chloroform
  4. additionmade basic with the addition of 2 M sodium carbonate
  5. customThe aqueous layer was separated
  6. extractionat extracted with chloroform (4×)
  7. washthe combined organic fractions were washed with brine
  8. extractionThe brine was extracted with chloroform (4×)
  9. dry with materialThe combined organic fractions were dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe crude product (8.08 g) was purified by chromatography on a HORIZON HPFC system (65I cartridge
  13. washeluting with chloroform/CMA in a gradient from 100:0 to 80:20)

Sources & evidence

ORD record
ord-3ef3cef56caf45d0ad7277b778f146cf
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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