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

HRID 1451976

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 etude 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 etude product
customPurification via flash column chromatography (silica gel, DCM)

Quellen und Nachweise

ORD-Eintrag: ord-3657eebc9e4441f093c1d8d583236da9
Quelldatensatz: uspto-grants-1997_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05605925

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