Trifluoroacetic acid → 4-[2-(4-Fluorophenoxy)ethyl]-1,3-thiazol-2-amine

HRID 1430640Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1430640
C(O)(C(F)(F)F)=O.C(OC(=O)[NH:14][C:15]1[S:16][CH:17]=[C:18]([CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[N:19]=1)(C)(C)C>C(Cl)Cl>[F:29][C:26]1[CH:25]=[CH:24][C:23]([O:22][CH2:21][CH2:20][C:18]2[N:19]=[C:15]([NH2:14])[S:16][CH:17]=2)=[CH:28][CH:27]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 59363813HCID 59363813, Verbindung

Produkt 1

HCID 20500224-[2-(4-Fluorophenoxy)ethyl]-1,3-thiazol-2-amineAusbeute 86,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

TFA (12 ml) was added to a solution of {4-[2-(4-Fluoro-phenoxy)-ethyl]-thiazol-2-yl}-carbamic acid tert-butyl ester (2.55 g, 7.5 mmol) in DCM (100 ml) at 0° C. and stirred at r.t. for 4 h. The reaction was quenched with saturated aqueous NaHCO3 solution (15 ml) and extracted in DCM, dried over Na2SO4, evaporated under reduced pressure to yield 4-[2-(4-Fluoro-phenoxy)-ethyl]-thiazol-2-ylamine (1.55 g, 86%). 1H NMR (400 MHz, CDCl3): δ 3.0 (t, J=6.8 Hz, 2H), 4.20 (t, J=6.8 Hz, 2H), 4.88 (brs, 2H), 6.26 (s, 1H), 6.83-6.86 (m, 2H), 6.94-6.98 (m, 2H).

Aufarbeitung

  1. customThe reaction was quenched with saturated aqueous NaHCO3 solution (15 ml)
  2. extractionextracted in DCM
  3. dry with materialdried over Na2SO4
  4. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c185f36c82554066960766b233b1bf96
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940900B2

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