Thionyl Chloride → 3-Chloro-3-(4-chlorophenyl)-2-(4-nitrobenzyl)isoindolin-1-one

HRID 1916978Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1916978
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[N:9]2[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[CH:4][CH:3]=1.S(Cl)([Cl:31])=O>CN(C=O)C>[Cl:31][C:8]1([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:17])[N:9]1[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 513497043-(4-Chlorophenyl)-3-hydroxy-2-(4-nitrobenzyl)isoindolin-1-one

Produkt 1

HCID 513494183-Chloro-3-(4-chlorophenyl)-2-(4-nitrobenzyl)isoindolin-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideKatalysator

Versuchsvorschrift

Distilled THF (10 mL) was added to 3-(4-chlorophenyl)-3-hydroxy-2-(4-nitrobenzyl)isoindolin-1-one (200 mg, 0.52 mmol), thionyl chloride (136.8 mg, 1.15 mmol, 0.08 mL) and catalytic DMF (3 drops) as for general procedure B1. 3-Chloro-3-(4-chlorophenyl)-2-(4-nitrobenzyl)isoindolin-1-one was produced as a viscous yellow oil (208.5 mg, 0.52 mmol) which was used immediately without further purification. Distilled THF (3 mL) was added to 3-chloro-3-(4-chlorophenyl)-2-(4-nitrobenzyl)isoindolin-1-one (208.5 mg, 0.52 mmol) and the resultant solution added dropwise to cis-cyclopentene diol (260 mg, 2.6 mmol) and dried potassium carbonate (359 mg, 2.6 mmol) in distilled THF (3 mL) as for general procedure B1. Removal of the solvent yielded the crude product as a yellow oil (262 mg). The sample was purified by flash column chromatography (EtOAc:Petrol, 40:60) to yield the title product as a yellow viscous oil. (211 mg, 44.4 mmol, 85%). 1H NMR: (300 MHz, DMSO) δ ppm 1.34, (m, 1H, H15/H16) 1.74, 2.2 (m, 1H, H15/H16) 4.22 (dt, 1H, H16) 4.40 (d, 1H, J=15.99 Hz, H9/H9′), 4.63 (d, 1H, J=16.02 Hz, H9/H9′), 4.93, 4.98, (dd, 1H, H17/H18), 5.15, 5.29 (dd, 1H, H17/H18), 5.76 (m, 1H, H14) 7.26 (m, 7H, H1-H5, H10, H13), 7.66 (m, 2H, H6-H7), 7.88 (d, 1H, H8), 8.00 (m, 2H, H11, H12).

Aufarbeitung

  1. distillationDistilled THF (10 mL)

Quellen und Nachweise

ORD-Eintrag
ord-5eee6ff7c1ae4cc69450951e902e8646
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618158B2

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