Ethyl 2-aminobenzoate → Ethyl 2-[3-(2-furyl)acrylamido]benzoate

HRID 1084822

Reaktionsgleichung

Reaktionsgleichung von HRID 1084822
[I-].ClC1C=CC=C[N+]=1C.[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH:15]=[CH:16][C:17]([OH:19])=O.C(N(CC)CC)C.[NH2:27][C:28]1[CH:38]=[CH:37][CH:36]=[CH:35][C:29]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31]>C(Cl)Cl>[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH:15]=[CH:16][C:17]([NH:27][C:28]1[CH:38]=[CH:37][CH:36]=[CH:35][C:29]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:19]

Komponenten

6

Edukt 4

HCID 6877Ethyl 2-aminobenzoateHCID 8471TriethylamineHCID 10876Furylacrylic acidHCID 1670692-Chloro-1-methylpyridinium iodide

Produkt 1

HCID 4450927Ethyl 2-[3-(2-furyl)acrylamido]benzoateAusbeute 30,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

Under nitrogen stream, 2-chloro-1-methylpyridinium iodide (1.272 g, 4.34 mmol) was suspended in dry methylene chloride (5 ml). To the suspension a solution of 3-(2-furyl)acrylic acid (500 mg, 3.62 mmol), triethylamine (1.2 ml, 8.69 mmol), and ethyl 2-aminobenzoate (0.53 ml, 3.62 mmol) in dry methylene chloride (5 ml) was added. The mixture was heated under reflux for 40 hours. Then, the reaction mixture was diluted with methylene chloride, and washed with 10% aqueous HCl, saturated aqueous sodium chloride, 1N-aqueous NaOH, and saturated aqueous sodium chloride successively, and dried. Removal of solvent gave a viscous oil, which, on washing with n-hexane gave white solids of the title compound (312 mg, yield: 30.2%), which was recrystallized from methanol. m.p., 85°-86° C.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 40 hours
  3. washwashed with 10% aqueous HCl, saturated aqueous sodium chloride, 1N-aqueous NaOH, and saturated aqueous sodium chloride successively
  4. customdried
  5. customRemoval of solvent
  6. customgave a viscous oil, which
  7. washon washing with n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-9cb8dfb2cb994905a60b3a6f3c499400
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05006548

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