Potassium Iodide → 5-Chloro-2-hydroxy-3-iodobenzaldehyde

HRID 849466Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 849466
[Cl:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.[I:11]N1C(=O)CCC1=O.IC1C=C(Br)C=C(C=O)C=1O.BrC1C=C(C=O)C(O)=CC=1.[I-].[K+].CC1C=CC(S(NCl)(=O)=O)=CC=1>CN(C=O)C.C(#N)C>[I:11][C:4]1[CH:3]=[C:2]([Cl:1])[CH:9]=[C:6]([CH:7]=[O:8])[C:5]=1[OH:10]

Komponenten

9

Edukt 6

HCID 4875Potassium IodideHCID 124815-Chloro-salicylaldehydeHCID 31388TosylchloramideHCID 728635-BromosalicylaldehydeHCID 120273N-IodosuccinimideHCID 27166955-Bromo-2-hydroxy-3-iodobenzaldehyde

Produkt 1

HCID 37725455-Chloro-2-hydroxy-3-iodobenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Scheme II illustrates methodology useful for preparing the ethyl N-gly-amino-3-(3,5-dihalo-2-hydroxy) phenyl propionate portion of the present invention which can be coupled to the tetrahydropyrimidinobenzoic acid moiety. Briefly, 3,5-halo substituted salicylaldehydes may be prepared by direct halogenation as, for example, would be the case where 5-bromosalicylaldehyde is slurried in acetic acid and an equivalent or more of chlorine is added to yield 3-chloro-5-bromo-2-hydroxybenzaldehyde. Some product precipitates and can be recovered by filtration. The remainder may be recovered by diluting the filtrate with water and isolating the precipitate. Combining the solids and drying gives 3-chloro-5-bromo-2-hydroxybenzaldehyde. 3-iodo-5-chlorosalicycaldehyde may be prepared by reacting 5-chlorosalicylaldehyde with N-iodosuccinimide in DMF and subjecting the reaction mixture to usual work-up conditions. 3-iodo-5-bromosalicylaldehyde may be prepared by reacting 5-bromosalicylaldehyde in acetonitrile with potassium iodide and chloramine T. Work-up gives a material that when treated with hexanes gives the desired 3-iodo-5-chlorosalicylaldehyde.

Aufarbeitung

  1. custom3-iodo-5-chlorosalicycaldehyde may be prepared
  2. customWork-up gives a material that when

Quellen und Nachweise

ORD-Eintrag
ord-f4aa2c426dc64ecebe71aa88f1283f00
Quelldatensatz
uspto-grants-2000_01
Patentnummer
US06013651

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