4-Chlorobenzoyl chloride → Methyl 4-{[(4-chlorobenzoyl)amino]methyl}benzoate

HRID 642090

Reaction equation

HRID 642090 reaction equation
[NH2:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[Cl:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1>C(Cl)Cl>[Cl:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH:1][CH2:2][C:3]2[CH:4]=[CH:5][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:11][CH:12]=2)=[O:19])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 85014-Chlorobenzoyl chlorideHCID 571728Methyl 4-(aminomethyl)benzoate

Product 1

HCID 60409609Methyl 4-{[(4-chlorobenzoyl)amino]methyl}benzoateYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of methyl 4-(aminomethyl)benzoate (75 g, 0.46 mol) and TEA (315 mL, 2.27 mol) in anhydrous DCM (1.5 L) was added a solution of freshly prepared 4-chloro benzoyl chloride (0.91 mol) in DCM (400 mL). The resulting mixture was allowed to stir for 12 hrs. The reaction was quenched with a 10% aqueous solution of sodium hydrogenocarbonate. The organic layer was washed with a 1.5N HCl solution and water. After drying over MgSO4 and evaporation of the solvent in vacuo, a solid was obtained. Recrystallization form MeOH gave the title compound (80 g) in a 60% yield as a white powder.

Workup

  1. customThe reaction was quenched with a 10% aqueous solution of sodium hydrogenocarbonate
  2. washThe organic layer was washed with a 1.5N HCl solution and water
  3. dry with materialAfter drying over MgSO4 and evaporation of the solvent in vacuo
  4. customa solid was obtained
  5. customRecrystallization
  6. customform MeOH

Sources & evidence

ORD record
ord-018a57b570714f0d83f16d6d6baeab08
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Linked notes

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