Chlorosuccinimide → HCID 66584727, compound

HRID 1629987Notes

Reaction equation

HRID 1629987 reaction equation
[C:1]1([C:7]2[C:8]([C:12]#[N:13])=[CH:9][NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:14]N1C(=O)CCC1=O>O1CCCC1>[Cl:14][C:11]1[NH:10][CH:9]=[C:8]([C:12]#[N:13])[C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 37214604-Phenyl-1H-pyrrole-3-carbonitrile

Product 1

HCID 66584727HCID 66584727, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 44.3 g (263 mmol) of 4-phenyl-1H-pyrrole-3-carbonitrile (CAS 40167-37-1) in 600 ml of tetrahydrofuran are added portionwise 35.8 g (268 mmol) of N-chlorosuccinimide (CAS 128-09-6) and the mixture is then stirred for 48 hours at reflux. After cooling, the reaction medium is concentrated under reduced pressure and the residue is then taken up in water. The reaction product is extracted with ethyl acetate, the organic phase is dried over sodium sulfate and the solvent is evaporated off under reduced pressure to give a brown solid, which is triturated in diisopropyl ether and then isolated by filtration. The filtrate is concentrated under reduced pressure and the solid residue obtained is triturated in diisopropyl ether and then isolated by filtration. The two batches of solid are combined to give 51.7 g of 5-chloro-4-phenyl-1H-pyrrole-3-carbonitrile in the form of a beige-coloured powder after drying.

Workup

  1. temperatureat reflux
  2. temperatureAfter cooling
  3. concentrationthe reaction medium is concentrated under reduced pressure
  4. extractionThe reaction product is extracted with ethyl acetate
  5. dry with materialthe organic phase is dried over sodium sulfate
  6. customthe solvent is evaporated off under reduced pressure
  7. customto give a brown solid, which
  8. customis triturated in diisopropyl ether
  9. customisolated by filtration
  10. concentrationThe filtrate is concentrated under reduced pressure
  11. customthe solid residue obtained
  12. customis triturated in diisopropyl ether
  13. customisolated by filtration

Sources & evidence

ORD record
ord-ce89a76415e74a80bdc5113b0ec5324e
Source dataset
uspto-grants-2014_07
Patent number
US08791119B2

Reaction notes

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