Hydrochloric Acid → HCID 19863414, compound

HRID 1164936Notes

Reaction equation

HRID 1164936 reaction equation
[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH2:6])[CH3:2].F[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1.[ClH:19]>C(Cl)Cl>[ClH:19].[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH:6][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9590p-FluoronitrobenzeneHCID 60993N,N-Diethylethylenediamine

Product 1

HCID 19863414HCID 19863414, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 8.3 g (71 mmol) of N,N-diethylethylenediamine under nitrogen atmosphere add 6.6 g (47 mmol) of 4-fluoronitrobenzene. Stir the mixture at ambient temperature for 1 day and heat at 45° C. for 4 h. Upon completion of the reaction add 100 mL of CH2Cl2 and 100 mL 1M HCl. Separate the layers and add 50% sodium hydroxide to the aqueous layer until it is basic. Extract the aqueous layer with 2×100 mL CH2Cl2, dry the organics over anhydrous Na2SO4. Remove drying agent by filtration and remove solvent in vacuo. Dissolve the residue in methanolic HCl and remove the solvent in vacuo. Recrystallize the solid from EtOH to afford the title compound.

Workup

  1. temperatureheat at 45° C. for 4 h
  2. customSeparate the layers
  3. additionadd 50% sodium hydroxide to the aqueous layer until it
  4. extractionExtract the aqueous layer with 2×100 mL CH2Cl2
  5. dry with materialdry the organics over anhydrous Na2SO4
  6. customRemove
  7. customdrying agent
  8. filtrationby filtration
  9. customremove solvent in vacuo
  10. dissolutionDissolve the residue in methanolic HCl
  11. customremove the solvent in vacuo
  12. customRecrystallize the solid from EtOH

Sources & evidence

ORD record
ord-617d86e3debf441cb9081c11dc6a34b0
Source dataset
uspto-grants-1990_03
Patent number
US04906634

Reaction notes

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