Hydrochloric Acid → HCID 15057241, compound

HRID 2073724Notes

Reaction equation

HRID 2073724 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.[CH2:18]=O.Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:18][N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 712FormaldehydeHCID 76690(3,4-Dichlorophenyl)acetonitrileHCID 212848Pyrrolidine, hydrochloride (1:1)

Product 1

HCID 15057241HCID 15057241, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 100 mL of ethanol is added (18.6 g (0.1 mol) 3,4-dichlorobenzeneacetonitrile, 12.6 g (0.12 mol) of pyrrolidine hydrochloride, 6.0 g (0.2 mol) of paraformaldehyde and 1 mL of concentrated hydrochloric acid. Stir the mixture at reflux. Monitor the progress of the reaction by thin-layer chromatography. Upon completion add 300 mL of 1N HCl and extract with 200 mL of Et2O. Add 4N NaOH to the aqueous solution until basic and extract the aqueous solution with two 100 mL portions of CH2Cl2. Dry the organic phase over anhydrous Na2SO4. Filter the drying agent and evaporate the solvent in vacuo to obtain the title compound.

Workup

  1. temperatureat reflux
  2. customMonitor the progress of the reaction by thin-layer chromatography
  3. extractionextract with 200 mL of Et2O
  4. additionAdd 4N NaOH to the aqueous solution until basic
  5. extractionextract the aqueous solution with two 100 mL portions of CH2Cl2
  6. dry with materialDry the organic phase over anhydrous Na2SO4
  7. filtrationFilter the drying agent
  8. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-96c639b7fd394e008888ccd707ce49d6
Source dataset
uspto-grants-1990_04
Patent number
US04920116

Reaction notes

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