Carbon Dioxide → HCID 15022347, Verbindung

HRID 1589987Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1589987
[Cl:1][C:2]1[C:3]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:8])=[CH:4][S:5][CH:6]=1.C([Li])CCC.[C:21](=[O:23])=[O:22]>C1COCC1>[Cl:1][C:2]1[C:3]([C:7]([NH:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:8])=[C:4]([C:21]([OH:23])=[O:22])[S:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 280Carbon DioxideHCID 15022346HCID 15022346, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 15022347HCID 15022347, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

4-Chlorothiophene-3-carboxanilide (14.6 g, 0.061 mol) is dissolved in 450 ml of THF and the solution is cooled to -70° C.; n-butyllithium (0.13 mol, 1.6N solution in n-hexane) is then added. After 30 minutes, carbon dioxide is gassed in until the solution was saturated, and the solution is allowed to heat up slowly to room temperature. It is then concentrated to dryness, the solid residue is taken up in a mixture of water, sodium hydroxide solution and ethyl acetate, the phases are separated and the aqueous phase is acidified with hydrochloric acid, thus precipitating the carboxylic acid. Yield: 13.5 g, 78%; m.p. 208°-210° C. (active ingredient no. 2.008).

Aufarbeitung

  1. temperatureto heat up slowly to room temperature
  2. concentrationIt is then concentrated to dryness
  3. additionthe solid residue is taken up in a mixture of water, sodium hydroxide solution and ethyl acetate
  4. customthe phases are separated
  5. customthus precipitating the carboxylic acid

Quellen und Nachweise

ORD-Eintrag
ord-504a0433cc944b5997c532a394f181b4
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05201934

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