HCID 18462172, compound → p-Anisic acid, 3-(bis(2-chloroethyl)amino)-

HRID 2304027Notes

Reaction equation

HRID 2304027 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([CH2:17][CH2:18][Cl:19])[C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:8]([O:10]C)=[O:9]>Cl>[Cl:1][CH2:2][CH2:3][N:4]([CH2:17][CH2:18][Cl:19])[C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:8]([OH:10])=[O:9]

Participants

3

Reactant 1

HCID 18462172HCID 18462172, compound

Product 1

HCID 32674p-Anisic acid, 3-(bis(2-chloroethyl)amino)-Yield 80%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of methyl 3-bis(2′-chloroethyl)amino-4-methoxybenzoate (2.70 g, 8.823 mmol) in concentrated HCl (37% w/w in H2O, 40 mL) was heated to reflux under N2 for 1 hour. The reaction mixture was treated with ice/H2O (200 mL), extracted with ethyl acetate (4×150 mL). The organic solution was concentrated to give a white solid (2.05 g, 80%). ESMS calcd for C12H15Cl2NO3: 291.0; Found: 292.0 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2 for 1 hour
  3. extractionextracted with ethyl acetate (4×150 mL)
  4. concentrationThe organic solution was concentrated

Sources & evidence

ORD record
ord-2c3694e21b5241108ee2ecebd2145f57
Source dataset
uspto-grants-2002_08
Patent number
US06433199B1

Reaction notes

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