Hydrochloric Acid → 7-Ethyl-2,3-dioxo-1,2,3,4-tetrahydrothieno[2,3-b]pyrazine-6-carboxylic acid

HRID 1974973Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1974973
C([O:3][C:4]([C:6]1[S:16][C:9]2[NH:10][C:11](=[O:15])[C:12](=[O:14])[NH:13][C:8]=2[C:7]=1[CH2:17][CH3:18])=[O:5])C.[OH-].[Na+].Cl.O>O1CCCC1>[C:4]([C:6]1[S:16][C:9]2[NH:10][C:11](=[O:15])[C:12](=[O:14])[NH:13][C:8]=2[C:7]=1[CH2:17][CH3:18])([OH:5])=[O:3]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 19100738HCID 19100738, Verbindung

Produkt 1

HCID 191007307-Ethyl-2,3-dioxo-1,2,3,4-tetrahydrothieno[2,3-b]pyrazine-6-carboxylic acidAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of 6-ethoxycarbonyl-7-ethylthieno[2,3-b]-pyrazine-2,3(1H,4H)-dione (24.5 g, 91 mmol) and sodium hydroxide (10.96 g, 274 mmol) in 50% aqueous tetrahydrofuran (340 ml) was heated at 50°-60° C. for 16 h. The reaction mixture was cooled to 0° C. and acidified (pH=2) with hydrochloric acid. Water (300 ml) was added, the precipitate filtered off, washed with water and dried. Purification was performed by dissolving in 2 M sodium hydroxide solution, extraction with dichloromethane and precipitation of the aqueous phase with hydrochloric acid. The precipitate was filtered off, washed with water and dried to afford 14.2 g (65%) of the title compound. M.p. 230°-232° C. 1H-NMR (DMSO-d6, δ) : 1. 09 (t, 3H) 3.03 (q, 2H), 11.90 (s, 1H), 12.50 (br. s, 1H), 12.92 (br. s, 1H).

Aufarbeitung

  1. temperaturewas heated at 50°-60° C. for 16 h
  2. filtrationthe precipitate filtered off
  3. washwashed with water
  4. customdried
  5. customPurification
  6. dissolutionby dissolving in 2 M sodium hydroxide solution
  7. extractionextraction
  8. customwith dichloromethane and precipitation of the aqueous phase with hydrochloric acid
  9. filtrationThe precipitate was filtered off
  10. washwashed with water
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-b31c7dc688a745e4adf4b86aef5bf2e3
Quelldatensatz
uspto-grants-1994_02
Patentnummer
US05284847

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