2-Amino-5-Nitrothiazole → 2-Bromo-N-(5-nitro-thiazol-2-yl)-acetamide

HRID 2243843

Reaktionsgleichung

Reaktionsgleichung von HRID 2243843
[NH2:1][C:2]1[S:3][C:4]([N+:7]([O-:9])=[O:8])=[CH:5][N:6]=1.C(=O)([O-])[O-].[Na+].[Na+].[Br:16][CH2:17][C:18](Br)=[O:19]>C(OCC)(=O)C>[Br:16][CH2:17][C:18]([NH:1][C:2]1[S:3][C:4]([N+:7]([O-:9])=[O:8])=[CH:5][N:6]=1)=[O:19]

Komponenten

5

Edukt 3

HCID 84862-Amino-5-NitrothiazoleHCID 10340Sodium CarbonateHCID 61147Bromoacetyl bromide2×

Produkt 1

HCID 3244582-Bromo-N-(5-nitro-thiazol-2-yl)-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-amino-5-nitrothiazole (725.7 mg) in ethyl acetate (50 mL) in the presence of saturated sodium carbonate (10 mL) at 0° C., is added bromoacetyl bromide (434.3 uL), and additional bromoacetyl bromide is added to complete the reaction. The organic layer is separated, washed with 3 N HCl solution, followed by brine and dried over sodium sulfate and concentrated in vacuo to give a brown oil. The crude product is purified by silica gel column chromatography (40% ethyl acetate/hexanes) to give a solid (950 mg). ESI MS m/z 266 (M+H+); 1H NMR (400 MHz, CDCl3) δ 8.26 (s, 1H), 3.98 (s, 2H).

Aufarbeitung

  1. additionis added
  2. customthe reaction
  3. customThe organic layer is separated
  4. washwashed with 3 N HCl solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give a brown oil
  8. customThe crude product is purified by silica gel column chromatography (40% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-ebc8c46a25d9422993c05280592c70ed
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07678791B2

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