Ethyl 2-aminobenzoate → HCID 898498, Verbindung

HRID 1084819Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1084819
[I-].ClC1C=CC=C[N+]=1C.[S: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>[S: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 928683-Thiophen-2-ylprop-2-enoic acidHCID 1670692-Chloro-1-methylpyridinium iodide

Produkt 1

HCID 898498HCID 898498, VerbindungAusbeute 45,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

Under nitrogen stream, 2-chloro-1-methylpyridinium iodide (966 mg, 3.89 mmol) was suspended in dry methylene chloride (5 ml). To the suspension, a solution of 3-(2-thienyl)acrylic acid (500 mg, 3.24 mmol), triethylamine (1.08 ml, 7.78 mmol), and ethyl 2-aminobenzoate (0.48 ml, 3.24 mmol) in dry methylene chloride (5 ml) was added dropwise. After the addition, the mixture was heated under reflux for 39 hours. Then, the reaction mixture was diluted with methylene chloride, 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 yellow solid, which was washed with n-hexane to give pale yellow solids of the title compound (442 mg, yield, 45%). m.p., 126°-127° C. (recrystallized from methanol)

Aufarbeitung

  1. additionAfter the addition
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 39 hours
  4. washwashed with 10% aqueous HCl, saturated aqueous sodium chloride, 1N-aqueous NaOH, and saturated aqueous sodium chloride successively
  5. customdried
  6. customRemoval of solvent
  7. customgave a yellow solid, which
  8. washwas washed with n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-f36049eb20524f8bafa9d902836017b1
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05006548

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