Methyl 3-(dimethylamino)acrylate → Methyl 4-(2,3-dichlorophenyl)-1H-pyrrole-3-carboxylate

HRID 1194120

Reaktionsgleichung

Reaktionsgleichung von HRID 1194120
Cl.[Cl:2][C:3]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5](=O)[CH2:6][NH2:7].CN(C)[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[O:19].CC[O-].[Na+]>C(O)C>[C:18]([C:17]1[C:5]([C:4]2[CH:9]=[CH:10][CH:11]=[C:12]([Cl:13])[C:3]=2[Cl:2])=[CH:6][NH:7][CH:16]=1)([O:20][CH3:21])=[O:19]

Komponenten

5

Edukt 3

HCID 566587Methyl 3-(dimethylamino)acrylateHCID 2723922Sodium ethoxideHCID 22151845Ethanone, 2-amino-1-(2,3-dichlorophenyl)-, hydrochloride

Produkt 1

HCID 15087831Methyl 4-(2,3-dichlorophenyl)-1H-pyrrole-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

10.7 g of 2,3-dichlorophenacylamine hydrochloride and 6 g of methyl 3-dimethylaminoacrylate are heated for 2 hours under reflux in 120 ml of ethanol. Then a solution of 4 g of sodium ethylate in 40 ml of ethanol is added dropwise and the reaction mixture is heated for another hour under reflux. The reaction mixture is then concentrated by evaporation and the oily residue is purified by column chromatography (silica gel; elution with a 3:1 mixture of toluene/ethyl acetate. Melting point: 205°-206° C.

Aufarbeitung

  1. temperaturethe reaction mixture is heated for another hour
  2. temperatureunder reflux
  3. concentrationThe reaction mixture is then concentrated by evaporation
  4. customthe oily residue is purified by column chromatography (silica gel
  5. washelution
  6. additionwith a 3:1 mixture of toluene/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-3aebb0837e574dcbbfacd7c488349763
Quelldatensatz
uspto-grants-1989_03
Patentnummer
US04812580

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