Carbon Dioxide → HCID 15022347, Verbindung

HRID 1197421Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1197421
[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]>O1CCCC1>[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 tetrahydrofuran, the solution is cooled to -70° C. and n-butyllithium (0.13 mol, 1.6N solution in n-hexane) is added. After 30 minutes, carbon dioxide gas is passed in until the solution is saturated, and the solution is allowed to warm up slowly to room temperature. It is worked up by evaporating to dryness, taking up the solid residue in a mixture of water, sodium hydroxide solution and ethyl acetate, separating the phases and acidifying the aqueous phase with hydrochloric acid. The carboxylic acid is precipitated. Yield: 13.5 g, 78%; mp. 208° to 210° C.

Aufarbeitung

  1. temperatureto warm up slowly to room temperature
  2. customby evaporating to dryness
  3. additionin a mixture of water, sodium hydroxide solution and ethyl acetate
  4. customseparating the phases
  5. customThe carboxylic acid is precipitated

Quellen und Nachweise

ORD-Eintrag
ord-916390a0cff248938766d6b8129c5294
Quelldatensatz
uspto-grants-1994_01
Patentnummer
US05276009

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