methyl 1H-pyrrole-3-carboxylate → Methyl 5-(3,4-Dichlorophenylthio)pyrrole-3-carboxylate

HRID 1980981Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1980981
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([O:8][CH3:9])=[O:7])=[CH:2]1.[Cl:10][C:11]1[CH:12]=[C:13]([S:18]Cl)[CH:14]=[CH:15][C:16]=1[Cl:17]>>[Cl:10][C:11]1[CH:12]=[C:13]([S:18][C:5]2[NH:1][CH:2]=[C:3]([C:6]([O:8][CH3:9])=[O:7])[CH:4]=2)[CH:14]=[CH:15][C:16]=1[Cl:17]

Komponenten

3

Edukt 2

HCID 12361759methyl 1H-pyrrole-3-carboxylateHCID 128785403,4-Dichlorobenzenesulfenyl chloride

Produkt 1

HCID 12897048Methyl 5-(3,4-Dichlorophenylthio)pyrrole-3-carboxylateAusbeute 104,2 %

Versuchsvorschrift

By the procedure of Example 23, methyl pyrrole-3-carboxylate (2.5 g., 20 mmoles) was reacted with 3,4-dichlorobenzenesulfenyl chloride (4.24 g., 20 mmoles) to yield crude product (6.3 g., oil). The crude was chromatographed on 250 g. of silica gel, with 125 ml. fractions of the ethyl acetate-1/hexane-5/5% acetic acid eluant collected. Fractions 2 to 6 were combined and evaporated to dryness to afford purified methyl 5-(3,4-dichlorophenylthio)pyrrole-3-carboxylate (2.76 g., m.p. 93°-96° C.).

Quellen und Nachweise

ORD-Eintrag
ord-069bff06f28041deb4ea229928b08d48
Quelldatensatz
uspto-grants-1985_04
Patentnummer
US04511576

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