Sodium Carbonate → Benzoic acid, p-(N-(2-chloroethyl)-N-ethylamino)-

HRID 1458724Notes

Reaction equation

HRID 1458724 reaction equation
[CH2:1]([N:3]([C:7]1[CH:14]=[CH:13][C:10](C#N)=[CH:9][CH:8]=1)[CH2:4][CH2:5][Cl:6])[CH3:2].[C:15](=[O:18])([O-])[O-:16].[Na+].[Na+]>C(O)C.Cl>[CH2:1]([N:3]([C:7]1[CH:14]=[CH:13][C:10]([C:15]([OH:16])=[O:18])=[CH:9][CH:8]=1)[CH2:4][CH2:5][Cl:6])[CH3:2]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 22096802HCID 22096802, compound

Product 1

HCID 16285Benzoic acid, p-(N-(2-chloroethyl)-N-ethylamino)-Yield 40%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of 2.5 g (12.0 mmol) of 4-[N-ethyl,N-(2-chloroethyl)amino]benzonitrile in 25 ml of ethanol, 25 ml of concentrated hydrochloric acid were added, followed by reflux under heat for 12 hours. The reaction mixture was allowed to cool down. Sodium carbonate was then added to basify the solution, followed by washing with chloroform. The water layer was acidified with concentrated hydrochloric acid and then extracted with chloroform. The solvent was distilled out under reduced pressure, followed by washing with IPA, whereby 1.1 g of white powder were obtained (yield: 40%).

Workup

  1. temperatureby reflux
  2. temperatureunder heat for 12 hours
  3. temperatureto cool down
  4. washby washing with chloroform
  5. extractionextracted with chloroform
  6. distillationThe solvent was distilled out under reduced pressure
  7. washby washing with IPA

Sources & evidence

ORD record
ord-26ad6a43bc3b474b83801a3afe9e6232
Source dataset
uspto-grants-1998_12
Patent number
US05852011

Reaction notes

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