Methyl 4-aminobenzoate → Methyl 4-{[4-(hexyloxy)benzoyl]amino}benzoate

HRID 642071

Reaktionsgleichung

Reaktionsgleichung von HRID 642071
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[CH2:12]([O:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>N1C=CC=CC=1>[CH2:12]([O:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=2)=[O:24])=[CH:21][CH:20]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Komponenten

4

Edukt 2

HCID 12082Methyl 4-aminobenzoateHCID 170235Benzoyl chloride, 4-(hexyloxy)-

Produkt 1

HCID 4933611Methyl 4-{[4-(hexyloxy)benzoyl]amino}benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of methyl 4-aminobenzoate (500 mg, 3.31 mmol) in anhydrous pyridine (10 mL) was added dropwise 4-(hexyloxy)benzoyl chloride (890 μL) at 0° C. After 5 min the temperature was allowed to warm up to rt. After 90 min aminomethyl resin (Polymers Laboratories PL-AMS, 1.93 mmol/g, 720 mg) was added and the resulting mixture was stirred overnight at rt. After filtration and rinsing the resin, water (125 mL) was added to the filtrate and a white solid precipated out. Filtration and washing with water gave a solid which was dried under vacuo at 60° C. overnight. The title compound (1073 mg) was obtained as a white solid (91%) in 99.7% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Aufarbeitung

  1. additionAfter 90 min aminomethyl resin (Polymers Laboratories PL-AMS, 1.93 mmol/g, 720 mg) was added
  2. filtrationAfter filtration
  3. washrinsing the resin, water (125 mL)
  4. additionwas added to the filtrate
  5. filtrationFiltration
  6. washwashing with water
  7. customgave a solid which
  8. customwas dried under vacuo at 60° C. overnight

Quellen und Nachweise

ORD-Eintrag
ord-d5e9e818b73545a4b2bf1fcb6163a0bc
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696231B2

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