Acetyl chloride → 2-(2-Acetyl-1H-pyrrol-1-yl)-1H-isoindole-1,3(2H)dione

HRID 22401

Reaktionsgleichung

[C:1](Cl)(=[O:3])[CH3:2].[Sn](Cl)(Cl)(Cl)Cl.[N:10]1([N:15]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]2=[O:25])[CH:14]=[CH:13][CH:12]=[CH:11]1>C(Cl)Cl>[C:1]([C:11]1[N:10]([N:15]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]2=[O:25])[CH:14]=[CH:13][CH:12]=1)(=[O:3])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a stirred solution of acetyl chloride (6.77 ml) in DCM (400 ml) was added tin (IV) chloride (11.14 ml) at -5° C., under nitrogen. 2-(1H-pyrrol-1-yl)-1H-isoindole-1,3(2H)dione (20.0 g) was then added portion-wise, keeping the temperature below 0° C. The reaction mixture was then stirred at 0° C. for 0.5 hour, at which time it was poured into ice water. The layers were separated and the aqueous phase was extracted with DCM. The combined organics were washed twice with 5% HCl (aq.) and dried (MgSO4). Filtration and concentration gave the crude product. Purification via flash column chromatography (silica gel, DCM) afforded 9.62 g of the product as a solid, m.p. 204°-205° C.

Aufarbeitung

customthe temperature below 0° C
customThe layers were separated
extractionthe aqueous phase was extracted with DCM
washThe combined organics were washed twice with 5% HCl (aq.)
dry with materialdried (MgSO4)
filtrationFiltration and concentration
customgave the crude product
customPurification via flash column chromatography (silica gel, DCM)

Quellen und Nachweise

ORD-Eintrag: ord-cab4923a9dcb4b90a0b864c5b1457ce1
Quelldatensatz: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05428053

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