Diethyl Ether → (s)-2-(4-Nitrophenyl)-1-(2-phenylthiazol-4-yl)ethanamine hydrobromide salt

HRID 60047

Reaktionsgleichung

Reaktionsgleichung von HRID 60047
[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.[C:24]([NH2:32])(=[S:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.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:32]=[C:24]([C:25]3[CH:30]=[CH:29][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 683563ThiobenzamideHCID 53778469(S)-tert-Butyl (4-bromo-1-(4-nitrophenyl)-3-oxobutan-2-yl)carbamate

Produkt 1

HCID 66704795(s)-2-(4-Nitrophenyl)-1-(2-phenylthiazol-4-yl)ethanamine hydrobromide saltAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of (S)-tert-butyl 4-bromo-1-(4-nitrophenyl)-3-oxobutan-2-ylcarbamate, 7, (1.62 g, 4.17 mmol) and thiobenzamide (0.63 g, 4.60 mmol) in CH3CN (5 mL) is refluxed for 24 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 1.2 g (67% yield) of the desired product. LC/MS ESI+ 326 (M+1).

Aufarbeitung

  1. temperatureis refluxed for 24 hours
  2. filtrationThe precipitate which forms is collected by filtration
  3. customThe solid is dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-3a32ee165ad640ecac7d97b578be1ecd
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440963B2

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