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3-(Bromoacetyl)benzoic acid → 4-(3-Carboxyacetyl-phenyl)-thiazole-2-carboxylic acid ethyl ester

HRID 1266780
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1266780
[CH2:1]([O:3][C:4]([C:6]1[S:7][CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17](Cl)=[O:18])[CH:12]=2)[N:10]=1)=[O:5])[CH3:2].Br[CH2:21][C:22]([C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27]([OH:29])=[O:28])=O.C(OCC)(=S)C(N)=O>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[S:7][CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17](=[O:18])[CH2:26][C:27]([OH:29])=[O:28])[CH:12]=2)[N:10]=1)=[O:5])[CH3:2].[CH2:1]([O:3][C:4]([C:6]1[S:7][CH:21]=[C:22]([C:24]2[CH:32]=[CH:31][CH:30]=[C:26]([C:27]([OH:29])=[O:28])[CH:25]=2)[N:10]=1)=[O:5])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 27568353-(Bromoacetyl)benzoic acidHCID 216137632-ethoxy-2-thioxoAcetamideHCID 865869654-(3-Chlorocarbonyl-phenyl)-thiazole-2-carboxylic acid ethyl ester

Produkt 2

HCID 697808034-(3-Carboxyacetyl-phenyl)-thiazole-2-carboxylic acid ethyl esterHCID 697810514-(3-Carboxy-phenyl)-thiazole-2-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

The 4-(3-carboxyacetyl-phenyl)-thiazole-2-carboxylic acid ethyl ester was prepared from 4-(3-chlorocarbonyl-phenyl)-thiazole-2-carboxylic acid ethyl ester [prepared by the following sequence: i.) A mixture of 3-(2-bromo-acetyl)-benzoic acid [CAS-no. 62423-73-8] (2.43 g) and ethyl thiooxamate [CAS-no. 16982-21-1] (1.6 g) in THF (40 mL) was heated to 60° C. for 4 h and then partitioned between EtOAc and brine. The organic layer was dried and evaporated and the residue was crystallized from EtOAc/hexane to give 4-(3-carboxy-phenyl)-thiazole-2-carboxylic acid ethyl ester (2.2 g) as off-white crystals, mp 225-228° C. ii.) This carboxylic acid (2.1 g) was heated with thionyl chloride in toluene and the resulting carboxylic acid chloride was used directly in the next step.] (2.24 g) and bis(trimethylsilyl)malonate with n-BuLi in ether at −60° C. to 0° C. according to general procedure K (method c2). The crude material was transformed into the title compound by stirring in isopropenyl acetate and conc. H2SO4 according to general procedure L (method a). Obtained as yellow oil (2.7 g).

Aufarbeitung

  1. customprepared by the following sequence
  2. custompartitioned between EtOAc and brine
  3. customThe organic layer was dried
  4. customevaporated
  5. customthe residue was crystallized from EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-a7b9dea0ca6f41308d72dee6aceaf3ba
Quelldatensatz
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06548495B2

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