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

HRID 642090

Reaktionsgleichung

Reaktionsgleichung von HRID 642090
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-018a57b570714f0d83f16d6d6baeab08
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696231B2

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