Ethyl thiooxamate → Ethyl 5-(3-bromobenzyl)-4-methylthiazole-2-carboxylate

HRID 517539

Reaktionsgleichung

Reaktionsgleichung von HRID 517539
Br[CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[CH:8]=1)[C:3](=O)[CH3:4].[NH2:14][C:15](=[S:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17]>CCO>[Br:13][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=1)[CH2:6][C:2]1[S:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:14][C:3]=1[CH3:4]

Komponenten

4

Edukt 2

HCID 2733398Ethyl thiooxamateHCID 623939183-Bromo-4-(3-bromophenyl)butan-2-one

Produkt 1

HCID 86711480Ethyl 5-(3-bromobenzyl)-4-methylthiazole-2-carboxylateAusbeute 42,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 3-bromo-4-(3-bromophenyl)butan-2-one (1.8 g, 5.9 mmol) and ethyl 2-amino-2-thioxoacetate (745 mg, 5.6 mmol) in EtOH (20 mL) was refluxed overnight. The solvent was removed and the residue was purified by silica gel column chromatography (EtOAc:Petroleum ether=1:5) to afford ethyl 5-(3-bromobenzyl)-4-methylthiazole-2-carboxylate as a light yellow solid (800 mg, 42.1%). MS (ES+) C14H14BrNO2S requires: 339, 341 found: 340[M+H]+, 342 [M+2+H]+(1:1).

Aufarbeitung

  1. temperaturewas refluxed overnight
  2. customThe solvent was removed
  3. customthe residue was purified by silica gel column chromatography (EtOAc:Petroleum ether=1:5)

Quellen und Nachweise

ORD-Eintrag
ord-b9e1a5fcec0d4727a7ff2f29d26f66be
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115120B2

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