Methyl 3-Bromopyruvate → Methyl 2-(4-phenyl-1,2,3-thiadiazol-5-yl)thiazole-4-carboxylate

HRID 1250204

Reaktionsgleichung

Reaktionsgleichung von HRID 1250204
[C:1]1([C:7]2[N:8]=[N:9][S:10][C:11]=2[C:12](=[S:14])[NH2:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:16][C:17](=O)[C:18]([O:20][CH3:21])=[O:19].C(=O)([O-])O.[Na+]>ClC1C=CC=CC=1>[C:1]1([C:7]2[N:8]=[N:9][S:10][C:11]=2[C:12]2[S:14][CH:16]=[C:17]([C:18]([O:20][CH3:21])=[O:19])[N:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 352524Methyl 3-BromopyruvateHCID 516892Sodium BicarbonateHCID 183275234-Phenyl-1,2,3-thiadiazole-5-carbothioamide

Produkt 1

HCID 18327521Methyl 2-(4-phenyl-1,2,3-thiadiazol-5-yl)thiazole-4-carboxylateAusbeute 48,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7964ChlorobenzeneLösungsmittel

Versuchsvorschrift

In 20 ml of chlorobenzene were dissolved 1.1 g (5.0 mmol) of 4-phenyl-1,2,3-thiadiazole-5-carbothioamide and 0.92 g (5.0 mmol) of methyl bromopyruvate. The solution thus obtained was stirred for 3 hours with heating under reflux. After the reaction was completed, the reaction mixture was cooled to room temperature, a saturated aqueous solution of sodium hydrogen carbonate was added thereto, and the objective product was extracted with ethyl acetate. The solvent was distilled off from the extract solution under a reduced pressure, and the residue was purified by silica gel column chromatography using 3:1 mixture of n-hexane and ethyl acetate. Thus, 0.74 g of the objective compound was obtained.

Aufarbeitung

  1. customThe solution thus obtained
  2. temperaturewith heating
  3. temperatureunder reflux
  4. extractionthe objective product was extracted with ethyl acetate
  5. distillationThe solvent was distilled off from the extract solution under a reduced pressure
  6. customthe residue was purified by silica gel column chromatography
  7. addition3:1 mixture of n-hexane and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-d8b0bb66c694467a803ec8faffd9340d
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06337341B1

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