Hydrochloric Acid → HCID 14627781, compound

HRID 1109557Notes

Reaction equation

HRID 1109557 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:5][N:6]([CH2:16][CH2:17]CC#N)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=1.[OH-:25].[Na+].[CH2:27]([OH:29])[CH3:28].Cl>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:5][N:6]([CH2:16][CH2:17][CH2:28][C:27]([OH:25])=[O:29])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 22401910HCID 22401910, compound

Product 1

HCID 14627781HCID 14627781, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-[N,N-bis-(3,4-dichlorobenzyl)amino]butyronitrile (1.95g), NaOH (2.0g) and ethanol (25ml) was stirred and heated to reflux for 6 hours under a nitrogen blanket. After cooling, the solvent was evaporated in vacuo to give a paste which was taken up in water (30ml), acidified with conc. HCl, stirred well and cooled in ice. The oil which had precipitated crystallised slowly. The crystals were filtered off, washed well with water, and recrystallised from dimethylformamide, diluted with a large volume of ether. The precipitated oil again crystallised slowly. The crystals were triturated with hot isopropanol, diluted with ether, collected by filtration and dried at 50°/1 mm to give the title compound as the hydrochloride salt. (1 .20g), m.p. 227-231° (decomp).

Workup

  1. temperatureheated
  2. temperatureto reflux for 6 hours under a nitrogen blanket
  3. temperatureAfter cooling
  4. customthe solvent was evaporated in vacuo
  5. customto give a paste which
  6. stirringstirred well
  7. temperaturecooled in ice
  8. customThe oil which had precipitated
  9. customcrystallised slowly
  10. filtrationThe crystals were filtered off
  11. washwashed well with water
  12. customrecrystallised from dimethylformamide
  13. additiondiluted with a large volume of ether
  14. customThe precipitated oil again crystallised slowly
  15. customThe crystals were triturated with hot isopropanol
  16. additiondiluted with ether
  17. filtrationcollected by filtration
  18. customdried at 50°/1 mm

Sources & evidence

ORD record
ord-f080d53296e3468e92075a1235b95092
Source dataset
uspto-grants-1994_06
Patent number
US05321047

Reaction notes

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