Adipic anhydride → 5-(4,5,7-Trifluorobenzothiazol-2-yl)pentanoic acid
Reaktionsgleichung
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[C:4]([F:10])[C:3]=1[SH:11].[C:12]1(=O)[O:19][C:17](=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13]1>CN1C(=O)CCC1.O>[F:8][C:7]1[C:2]2[N:1]=[C:12]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[S:11][C:3]=2[C:4]([F:10])=[CH:5][C:6]=1[F:9]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
A solution of adipic acid (10.0 g, 68 mmol) in acetic anhydride (50 ml) was heated to reflux for 3 hours. An excess of acetic anhydride was then distilled off in vacuo leaving adipic anhydride (7.4 g). 2-Amino-3,4,6-trifluorothiophenol (200 mg, 1.1 mmol) was dissolved in NMP (1 ml) under a nitrogen stream. To the resultant solution was gradually added adipic anhydride (143 mg, 1.1 mmol) and the mixture was stirred at 100° C. for 6 hours. After naturally cooling, the mixture was diluted with water and extracted with ethyl acetate. The organic phase was extracted with aqueous sodium bicarbonate. The alkaline phase was acidified with 10% hydrochloric acid and re-extracted with ethyl acetate. The combined organic phases were dried and then evaporated to yield a residue, which was recrystallized from acetonitrile to give 5-(4,5,7-trifluorobenzothiazol-2-yl)pentanoic acid (81 mg, 26%).
Aufarbeitung
- temperatureAfter naturally cooling
- extractionextracted with ethyl acetate
- extractionThe organic phase was extracted with aqueous sodium bicarbonate
- extractionre-extracted with ethyl acetate
- customThe combined organic phases were dried
- customevaporated
- customto yield a residue, which
- customwas recrystallized from acetonitrile
Quellen und Nachweise
- ORD-Eintrag
- ord-7005869c31324fee9304fd0ffd3413f0
- Quelldatensatz
- uspto-grants-1997_12
- Patentnummer
- US05700819
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