Hydrochloric Acid → Benzoic acid, m-(bis(2-chloroethyl)amino)-

HRID 1458687Notes

Reaction equation

HRID 1458687 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][N:5]([C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=1)[C:12]([O:14]C)=[O:13])[CH2:6][CH2:7][Cl:8]>O>[Cl:2][CH2:3][CH2:4][N:5]([C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=1)[C:12]([OH:14])=[O:13])[CH2:6][CH2:7][Cl:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 32688Benzoic acid, m-(bis(2-chloroethyl)amino)-, methyl ester

Product 1

HCID 18332Benzoic acid, m-(bis(2-chloroethyl)amino)-Yield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Concentrated hydrochloric acid (40 ml) was added to 2.0 g (7.44 mmol) of methyl 3-[N,N-bis(2-chloroethyl)amino]benzoate, followed by stirring under heating for 3 hours over an oil bath which was controlled at 90° C. The reaction mixture was diluted with water. The resulting crystals were collected by filtration and then washed with 50% ethanol, whereby 1.95 g (7.44 mmol) of the title compound were obtained as white crystals (yield: quantitative).

Workup

  1. temperatureunder heating for 3 hours over an oil bath which
  2. customwas controlled at 90° C
  3. filtrationThe resulting crystals were collected by filtration
  4. washwashed with 50% ethanol

Sources & evidence

ORD record
ord-8365445a8c204108bf4e48374bba2a97
Source dataset
uspto-grants-1998_12
Patent number
US05852011

Reaction notes

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