5-(2-Methoxy-4-nitro-phenyl)-2-methyl-thiazole → 3-Methoxy-4-(2-methyl-thiazol-5-yl)-phenylamine

HRID 2076127Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2076127
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[C:12]1[S:16][C:15]([CH3:17])=[N:14][CH:13]=1>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([NH2:9])[CH:6]=[CH:5][C:4]=1[C:12]1[S:16][C:15]([CH3:17])=[N:14][CH:13]=1

Komponenten

3

Edukt 1

HCID 670963525-(2-Methoxy-4-nitro-phenyl)-2-methyl-thiazole

Produkt 1

HCID 670959033-Methoxy-4-(2-methyl-thiazol-5-yl)-phenylamineAusbeute 91,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A suspension of 5-(2-methoxy-4-nitro-phenyl)-2-methyl-thiazole (330 mg, 1.32 mmol) and anhydrous stannous chloride (1.28 g, 6.59 mmol) in ethanol (21 mL) was stirred at reflux for 1 hour. The yellow solution is evaporated and the residue dissolved in ethyl acetate. This solution is washed twice with 2N aqueous sodium hydroxide solution, with brine, dried with magnesium sulfate and evaporated to dryness to afford the title compound (266 mg, 91%) as an orange solid. MS ISP (m/e): 221.2 (100) [(M+H)]. 1H NMR (CDCl3, 300 MHz): δ(ppm)=7.81 (s, 1H), 7.33 (d, 1H), 6.31 (m, 2H), 3.87 (s, 3H), 3.83 (m, 2H), 2.69 (s, 3H). mp 125-129° C.

Aufarbeitung

  1. temperatureat reflux for 1 hour
  2. customThe yellow solution is evaporated
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washThis solution is washed twice with 2N aqueous sodium hydroxide solution, with brine
  5. dry with materialdried with magnesium sulfate
  6. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-d3de0e7fd8ab4530b258311813ed68ea
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07923450B2

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