Hydrochloric Acid → 4-(Bis(2-chloroethyl)amino)benzeneacetic acid

HRID 1458696Notes

Reaction equation

HRID 1458696 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][N:5]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([O:18]C)=[O:17])=[CH:11][CH:10]=1)[CH2:6][CH2:7][Cl:8]>O>[Cl:2][CH2:3][CH2:4][N:5]([C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:13][CH:14]=1)[CH2:6][CH2:7][Cl:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22096817methyl 4-[N,N-bis(2-chloroethyl)amino]phenylacetate

Product 1

HCID 253064-(Bis(2-chloroethyl)amino)benzeneacetic acidYield 84.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Concentrated hydrochloric acid (10 ml) was added to 2.0 g (6.9 mmol) of methyl 4-[N,N-bis(2-chloroethyl)amino]phenylacetate, followed by stirring under heat for 1 hour over an oil bath controlled at 90° C. The reaction mixture was diluted with water and was then extracted three times with methylene chloride. As the raw material still remained, the reaction product was extracted with a 1N aqueous solution of sodium hydroxide. The water layer was acidified with hydrochloric acid and then extracted again with methylene chloride. The extract was dried and concentrated under reduced pressure. The residue so obtained was washed with n-hexane, whereby 1.61 g (5.83 mmol) of the title compound were obtained as white crystals (yield: 84.5%).

Workup

  1. temperatureunder heat for 1 hour over an oil bath
  2. customcontrolled at 90° C
  3. extractionwas then extracted three times with methylene chloride
  4. extractionthe reaction product was extracted with a 1N aqueous solution of sodium hydroxide
  5. extractionextracted again with methylene chloride
  6. customThe extract was dried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue so obtained
  9. washwas washed with n-hexane

Sources & evidence

ORD record
ord-2f375f6fbe094eb9b262ef8b917ce584
Source dataset
uspto-grants-1998_12
Patent number
US05852011

Reaction notes

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