Trifluoroacetic acid → Trifluoroacetic acid

HRID 408494Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 408494
C(OC(=O)[NH:7][C:8]1[S:9][C:10]([CH:13](O)[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH3:22])=[CH:11][N:12]=1)(C)(C)C.C([SiH](CC)CC)C.[F:32][C:33]([F:38])([F:37])[C:34]([OH:36])=[O:35]>ClCCl>[CH3:22][O:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH2:14][CH2:13][C:10]1[S:9][C:8]([NH2:7])=[N:12][CH:11]=1.[F:32][C:33]([F:38])([F:37])[C:34]([OH:36])=[O:35]

Komponenten

6

Edukt 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58609916{5-[1-Hydroxy-2-(2-methoxy-phenyl)-ethyl]-thiazol-2-yl}-carbamic acid tert-butyl ester

Produkt 2

HCID 6422Trifluoroacetic acidAusbeute 42 %HCID 867128295-[2-(2-Methoxy-phenyl)-ethyl]-thiazol-2-ylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of {5-[1-Hydroxy-2-(2-methoxy-phenyl)-ethyl]-thiazol-2-yl}-carbamic acid tert-butyl ester (28 g, 0.080 mol), triethylsilane (130 g, 1.12 mol) and trifluoroacetic acid (250 g, 2.24 mol) in dichloromethane (500 mL) was stirred at room temperature for 15 hours. The mixture was evaporated to dryness and then stirred in water. The solid was filtered and washed with ether to give 5-[2-(2-Methoxy-phenyl)-ethyl]-thiazol-2-ylamine as a trifluoracetic acid salt (11 g, 0.033 mol, yield 42%). ESI-MS m/z cacl. 234.08. found 235.16 (M+1)+ 1H NMR (CDCl3) δ 8.81 (br, 2H), 7.20 (t, 1H), 7.12 (d, 1H), 6.95 (m, 2H), 6.85 (t, 1H), 3.76 (s, 3H), 2.83 (d, 2H), 2.80 (d, 2H).

Aufarbeitung

  1. customThe mixture was evaporated to dryness
  2. stirringstirred in water
  3. filtrationThe solid was filtered
  4. washwashed with ether

Quellen und Nachweise

ORD-Eintrag
ord-2e5b832b264c43ff8e8bfb454de3c6a7
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759335B2

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