Triethylamine → HCID 67258204, Verbindung

HRID 2371042Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2371042
[Br:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH:7](O)[CH2:8][N+:9]([O-:11])=[O:10].CCN(CC)CC.CS(Cl)(=O)=O>CN(C1C=CN=CC=1)C.C(Cl)Cl.O>[Br:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1/[CH:7]=[CH:8]/[N+:9]([O-:11])=[O:10]

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67256195HCID 67256195, Verbindung

Produkt 1

HCID 67258204HCID 67258204, VerbindungAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-(2-bromothiophen-3-yl)-2-nitroethanol (3 g, 12.0 mmol), DMAP (146 mg, 1.2 mmol) and Et3N (2.4 g, 24.0 mmol) in DCM (30 mL) was added MsCl (2.4 g, 24.0 mmol) dropwise. The resulting mixture was then refluxed for 3 h. After cooling, the reaction mixture was diluted with water and extracted with DCM. The combined organic layers were washed with brine and dried over anhydrous Na2SO4. After filtration and concentration, the crude product was purified by column chromatography to give the title compound (2.5 g, 88%).

Aufarbeitung

  1. temperatureThe resulting mixture was then refluxed for 3 h
  2. temperatureAfter cooling
  3. extractionextracted with DCM
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationAfter filtration and concentration
  7. customthe crude product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8f2f7dadcfb54f70a3ac5351c3838360
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08710245B2

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