Hydrogen Bromide → 2-Bromo-6-methoxy-1,3-benzothiazole

HRID 234703

Reaktionsgleichung

Reaktionsgleichung von HRID 234703
N[C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.N([O-])=O.[Na+].[BrH:17]>O.[Cu]Br>[Br:17][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1

Komponenten

6

Edukt 3

HCID 260Hydrogen Bromide2×HCID 156302-Amino-6-methoxybenzothiazoleHCID 23668193Sodium Nitrite

Produkt 1

HCID 112187652-Bromo-6-methoxy-1,3-benzothiazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24593copper(I) bromideKatalysatorHCID 962WaterLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Slurry 2-amino-6-methoxybenzothiazole (0.255mol) in water (325mL), heat to reflux and add 48% hydrobromic acid (130mL). Maintain at reflux for 20 minutes, cool to 0° C. and add a solution of sodium nitrite (17.56g, 0.255mol) in water (90mL), maintaining a temperature of 0° C. Stir at 0° C. for 15 minutes and add by dropwise addition (while keeping cold) to a rapidly stirring mixture of copper (I) bromide (42.03g,0.293mol) in 48% hydrobromic acid (86mL) and water (225mL). Stir at room temperature for 20 minutes. Allow to stand overnight, extract into methylene chloride and dry (MgSO4). Evaporate the solvent in vacuo and purify by chromatography to give 2-bromo-6-methoxybenzothiazole.

Aufarbeitung

  1. temperatureto reflux
  2. temperatureMaintain
  3. temperatureat reflux for 20 minutes
  4. temperaturemaintaining a temperature of 0° C
  5. additionadd by dropwise addition (while keeping cold) to
  6. stirringa rapidly stirring
  7. stirringStir at room temperature for 20 minutes
  8. waitAllow to stand overnight
  9. extractionextract into methylene chloride
  10. dry with materialdry (MgSO4)
  11. customEvaporate the solvent in vacuo
  12. custompurify by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fd3ff338436c43c09da4a75988d6b96c
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05596003

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