Diethyl Ether → (S)-2-(4-nitrophenyl)-1-(thiophen-2-ylthiazol-4-yl)ethanamine hydrobromide salt

HRID 335016

Reaktionsgleichung

Reaktionsgleichung von HRID 335016
[Br:1][CH2:2][C:3](=O)[C@@H:4]([NH:15]C(=O)OC(C)(C)C)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1.[S:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[C:29](=[S:31])[NH2:30].C(OCC)C>CC#N>[BrH:1].[N+:12]([C:9]1[CH:8]=[CH:7][C:6]([CH2:5][C@@H:4]([C:3]2[N:30]=[C:29]([C:25]3[S:24][CH:28]=[CH:27][CH:26]=3)[S:31][CH:2]=2)[NH2:15])=[CH:11][CH:10]=1)([O-:14])=[O:13]

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 7372372-ThiophenecarbothioamideHCID 53778469(S)-tert-Butyl (4-bromo-1-(4-nitrophenyl)-3-oxobutan-2-yl)carbamate

Produkt 1

HCID 66704718(S)-2-(4-nitrophenyl)-1-(thiophen-2-ylthiazol-4-yl)ethanamine hydrobromide saltAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of (S)-tert-butyl 4-bromo-1-(4-nitrophenyl)-3-oxobutan-2-ylcarbamate, 7, (7.74 g, 20 mmol), and thiophen-2-carbothioic acid amide (3.14 g, 22 mmol) in CH3CN (200 mL) is refluxed for 5 hours. The reaction mixture is cooled to room temperature and diethyl ether (50 mL) is added to the solution. The precipitate which forms is collected by filtration. The solid is dried under vacuum to afford 7.14 g (87% yield) of the desired product. ESI+ MS 332 (M+1).

Aufarbeitung

  1. temperatureis refluxed for 5 hours
  2. filtrationThe precipitate which forms is collected by filtration
  3. customThe solid is dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-5067efa4c7a84917975dbe308d67e92b
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883832B2

Verknüpfte Notizen

Wird geladen…