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

HRID 1855504

Reaktionsgleichung

Reaktionsgleichung von HRID 1855504
[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, 6.6 mmol) in ethanol (21 mL) was stirred at reflux for one hour. The yellow solution was evaporated and the residue dissolved in ethyl acetate. This solution was 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 [(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 one hour
  2. customThe yellow solution was evaporated
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washThis solution was 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-594a650122d548a3b36daccf2611566b
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962834B2

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