Reaktion #51828

ord-34198016cd934b30945836604352d606

Reaktionsgleichung

C[N+](C)(C)Cc1ccccc1.C[N+](C)(C)Cc1ccccc1.C[N+](C)(C)Cc1ccccc1.[Br-].[Br-].[Br-]
benzyl-trimethylammonium tribromide
CCN(c1nc(C)cs1)c1ccc(Cl)cc1Cl.Cl
2-(N-ethyl-2,4-dichloroanilino)-4-methylthiazole hydrochloride
O=C([O-])[O-].[Ca+2]
calcium carbonate
ClC(Cl)Cl
chloroform
CCN(c1nc(C)c(Br)s1)c1ccc(Cl)cc1Cl
5-bromo-2-(N-ethyl-2,4-dichloroanilino)-4-methyl-thiazole
Ausbeute 117.9%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONwas added
  2. 2
    FiltrationThe solids in the reaction mixture were filtered off
  3. 3
    Einengenthe filtrate was concentrated under reduced pressure
  4. 4
    SonstigeThe residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane-ethyl acetate=9:1)

Vorschrift

After 2-(N-ethyl-2,4-dichloroanilino)-4-methylthiazole hydrochloride (6.0 g) and calcium carbonate (4.6 g) were suspended in a mixed solvent of chloroform (90 mL) and methanol (36 mL), benzyl-trimethylammonium tribromide (7.2 g) was added thereto in small portions. The solids in the reaction mixture were filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane-ethyl acetate=9:1) to obtain 5-bromo-2-(N-ethyl-2,4-dichloroanilino)-4-methyl-thiazole (4.5 g).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06852732B2uspto-grants-2005_02