Hydrochloric Acid → HCID 18973026, Verbindung

HRID 2394336Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2394336
[Na].[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][N:11]=1)[NH:8][C:7](=[O:12])[CH2:6]2.[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[C:18](OCC)=[O:19].Cl>C(O)C>[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][N:11]=1)[NH:8][C:7](=[O:12])[CH:6]2[C:18](=[O:19])[C:14]1[S:13][CH:17]=[CH:16][CH:15]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 76052Ethyl 2-thenoateHCID 5360545Sodium2×HCID 189730325-Chloro-1,3-dihydro-2H-pyrrolo[2,3-c]pyridin-2-one

Produkt 1

HCID 18973026HCID 18973026, VerbindungAusbeute 34,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Pellets of sodium metal (232 mg, 10 mmol) were added to dry ethanol (10 mL) in a dry round-bottomed flask. When dissolution of the sodium was complete, solid 5-chloro-6-azaoxindole (340 mg, 2.0 mmol) was added followed by ethyl 2-thiophenecarboxylate (0.54 mL, 4.0 mmol). The mixture was heated under nitrogen at reflux overnight during which a precipitate formed. The mixture was cooled, poured into ice/water and acidified to pH 4 with 6N HCl solution. The solid product (475 mg) was collected by filtration, washed with water, and dried in the air. This material was recrystallized from methanol to afford the title compound (190 mg, 34%). 1H NMR (DMSO-d6): δ10.62 (br s, 1H), 8.79 (d, J=3.2 Hz, 1H), 7.92 (s, 1H), 7.77 (d, J=5 Hz, 1H), 7.65 (s, 1H), 7.17-7.14 (m, 1H).

Aufarbeitung

  1. temperatureThe mixture was heated under nitrogen
  2. temperatureat reflux overnight during which a precipitate
  3. customformed
  4. temperatureThe mixture was cooled
  5. filtrationThe solid product (475 mg) was collected by filtration
  6. washwashed with water
  7. customdried in the air
  8. customThis material was recrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-9ea4e84eadc74b05a774315ddac21b67
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05811432

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