Hydrogen Bromide → 1-(5-Bromo-6-hydroxy-1,3-benzothiazol-2-yl)-3-ethyl-urea

HRID 1399973Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1399973
[Br:1][C:2]1[C:3]([O:17]C)=[CH:4][C:5]2[S:9][C:8]([NH:10][C:11]([NH:13][CH2:14][CH3:15])=[O:12])=[N:7][C:6]=2[CH:16]=1.Br.[OH-].[Na+]>>[Br:1][C:2]1[C:3]([OH:17])=[CH:4][C:5]2[S:9][C:8]([NH:10][C:11]([NH:13][CH2:14][CH3:15])=[O:12])=[N:7][C:6]=2[CH:16]=1

Komponenten

4

Edukt 3

HCID 260Hydrogen Bromide2×HCID 14798Sodium HydroxideHCID 596030851-(5-Bromo-6-methoxy-1,3-benzothiazol-2-yl)-3-ethyl-urea

Produkt 1

HCID 898069531-(5-Bromo-6-hydroxy-1,3-benzothiazol-2-yl)-3-ethyl-urea

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Intermediate 6 (1.30 g, 3.94 mmol) was suspended in hydrogen bromide solution (6.82 mL, 47% aq., 59.1 mmol) and the resulting suspension warmed to 110° C. Hydrogen bromide solution (14 mL, 47% aq., 121.3 mmol) was added portion-wise over the course of the reaction. After 47 h, the reaction mixture was cooled to RT then in ice and the pH adjusted with sodium hydroxide solution (1 M, aq.) to pH 8. The mixture was filtered and the resulting solid washed with H2O and ACN. The solid was sucked dry to give i (1.01 g, 81%). MS 315.87 & 317.84 [M+H]+.

Aufarbeitung

  1. customover the course of the reaction
  2. temperaturethe reaction mixture was cooled to RT
  3. filtrationThe mixture was filtered
  4. washthe resulting solid washed with H2O and ACN
  5. customThe solid was sucked dry
  6. customto give i (1.01 g, 81%)

Quellen und Nachweise

ORD-Eintrag
ord-10620affaffa455f9b56b0d9b686d904
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906902B2

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