HCID 19956226, compound → HCID 19956218, compound

HRID 1779486Notes

Reaction equation

HRID 1779486 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:15]2[CH:19]=[CH:18][CH:17]=[CH:16]2)=[C:6]([CH:14]=1)[C:7](N1CCCC1)=[O:8]>P(Cl)(Cl)(Cl)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:15]3[CH:16]=[CH:17][CH:18]=[C:19]3[C:7](=[O:8])[C:6]=2[CH:14]=1

Participants

3

Reactant 1

HCID 19956226HCID 19956226, compound

Product 1

HCID 19956218HCID 19956218, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A solution of 8.5 g (30.9 mmol) of N-[5-chloro-2-(pyrrol-1-yl)benzoyl]pyrrolidine (Preparation 23) in 70 ml of phosphorus oxychloride is heated at 100° C. for 35 minutes. After cooling, the precipitate formed is isolated by filtration, washed with petroleum ether to remove excess phosphorus oxychloride, and then redissolved in 30 ml of water. The aqueous solution is rendered alkaline by the dropwise addition of 10% sodium hydroxide solution and the precipitate formed is filtered and extracted with 100 ml of ethyl acetate. The organic phase is washed with water, dried over magnesium sulfate, rendered colourless with animal charcoal and concentrated under reduced pressure to yield 1.76 g of the title product.

Workup

  1. temperatureAfter cooling
  2. customthe precipitate formed
  3. customis isolated by filtration
  4. washwashed with petroleum ether
  5. customto remove excess phosphorus oxychloride
  6. dissolutionredissolved in 30 ml of water
  7. additionby the dropwise addition of 10% sodium hydroxide solution
  8. customthe precipitate formed
  9. filtrationis filtered
  10. extractionextracted with 100 ml of ethyl acetate
  11. washThe organic phase is washed with water
  12. dry with materialdried over magnesium sulfate
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-41a72cd335f742259104f62051699aae
Source dataset
uspto-grants-1997_05
Patent number
US05627203

Reaction notes

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