Sodium Azide → 6-(2-Azido-ethoxy)-2-methyl-3-(4-trifluoromethyl-phenyl)-benzo[b]thiophene
Reaktionsgleichung
[CH3:1][C:2]1[S:6][C:5]2[CH:7]=[C:8]([O:11][CH2:12][CH2:13]OS(C)(=O)=O)[CH:9]=[CH:10][C:4]=2[C:3]=1[C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=1.[N-:29]=[N+:30]=[N-:31].[Na+]>CN(C)C=O>[N:29]([CH2:13][CH2:12][O:11][C:8]1[CH:9]=[CH:10][C:4]2[C:3]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)=[C:2]([CH3:1])[S:6][C:5]=2[CH:7]=1)=[N+:30]=[N-:31]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
0.300 g (0.697 mmol) Methanesulfonic acid 2-[2-methyl-3-(4-trifluoromethyl-phenyl)-benzo[b]thiophen-6-yloxy]-ethyl ester dissolved in 2.0 ml of N,N-dimethylformamide were treated with 0.137 g (2.09 mmol) sodium azide and the reaction mixture heated to 80° C. for 1 hour. It was then cooled to room temperature, poured into 30 ml of ice-water and extracted 3 times with 10 ml of ether. The combined ether phases were washed with brine, dried over magnesium sulfate and evaporated under reduced pressure giving 0.262 g (99.6%) 6-(2-Azido-ethoxy)-2-methyl-3-(4-trifluoromethyl-phenyl)-benzo[b]thiophene as colorless oil, MS: 377 (M+).
Aufarbeitung
- temperatureIt was then cooled to room temperature
- extractionextracted 3 times with 10 ml of ether
- washThe combined ether phases were washed with brine
- dry with materialdried over magnesium sulfate
- customevaporated under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-8bee3bc9fd3c4fdba23830f1c6649f23
- Quelldatensatz
- uspto-grants-2008_11
- Patentnummer
- US07449483B2
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