Chloroform → 4-Nitrophenyl (7-Isopropoxycarbonyl-6-methyl-2,3,5,6-tetrahydropyrrolo[2,1-b]thiazol-3-ylidene)acetate

HRID 2372377Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2372377
[CH3:1][CH:2]1[CH2:6][NH:5][C:4](=[S:7])[CH:3]1[C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9].C([O-])(=O)C.[Na+].Br[CH2:20][C:21](=O)[CH2:22][C:23]([O:25][C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=1)=[O:24].C(Cl)(Cl)Cl>C1C=CC=CC=1>[CH:11]([O:10][C:8]([C:3]1[CH:2]([CH3:1])[CH2:6][N:5]2[C:21](=[CH:22][C:23]([O:25][C:26]3[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=3)=[O:24])[CH2:20][S:7][C:4]=12)=[O:9])([CH3:13])[CH3:12]

Komponenten

6

Edukt 4

HCID 6212ChloroformHCID 517045Sodium AcetateHCID 10465433Isopropyl 4-Methyl-2-thioxopyrrolidine-3-carboxylateHCID 19903380HCID 19903380, Verbindung

Produkt 1

HCID 867455674-Nitrophenyl (7-Isopropoxycarbonyl-6-methyl-2,3,5,6-tetrahydropyrrolo[2,1-b]thiazol-3-ylidene)acetateAusbeute 66,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

8.9 g of isopropyl 4-methyl-2-thioxopyrrolidine-3-carboxylate was dissolved in 200 ml of benzene and 5.1 g of anhydrous sodium acetate and 16.7 g of 4-nitrophenyl 4-bromoacetoacetate were added thereto. The obtained mixture was stirred at room temperature for 8 hours. Then 500 ml of chloroform was added and the mixture was washed with water and a saturated aqueous solution of sodium chloride. After drying and distilling off the solvent, the obtained residue was purified by silica gel column chromatography. A fraction eluted with dichloromethane was crystallized from a mixture of ether and n-hexane. Thus 11.9 g of the title compound was obtained.

Aufarbeitung

  1. washthe mixture was washed with water
  2. customAfter drying
  3. distillationdistilling off the solvent
  4. customthe obtained residue was purified by silica gel column chromatography
  5. washA fraction eluted with dichloromethane
  6. customwas crystallized from a mixture of ether and n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-ca74665c805842a6a1a8e71e7009738f
Quelldatensatz
uspto-grants-1992_03
Patentnummer
US05098919

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