3',4'-Dimethoxycinnamic acid → 3,4-Dimethoxycinnamoylchloride

HRID 36923

Reaktionsgleichung

Reaktionsgleichung von HRID 36923
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH:6]=[CH:7][C:8](O)=[O:9].C(Cl)(=O)C([Cl:19])=O>CN(C=O)C.O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH:6]=[CH:7][C:8]([Cl:19])=[O:9]

Komponenten

5

Edukt 2

HCID 168483',4'-Dimethoxycinnamic acidHCID 65578Oxalyl chloride

Produkt 1

HCID 533992063,4-Dimethoxycinnamoylchloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 3,4-dimethoxycinnamic acid (540 mg), DMF (2 drops) and tetrahydrofuran (10 ml) was added oxalyl chloride (0.27 ml) dropwise. The mixture was stirred at room temperature for 40 minutes, at the end of which time the solvent was distilled off to give 3,4-dimethoxycinnamoyl chloride. The chloride was dissolved in dichloromethane (10 ml) followed by addition of 3-amino-4-(2-methylphenyl)-7,8-dihydrocyclopenta [g] [1]benzopyran-2(6H)-one (582 mg) and N,N-dimethylaniline (0.25 ml). The mixture was then stirred at room temperature for 20 hours, after which it was washed with water, dried (MgSO4) and distilled to remove the solvent. The residue was chromatographed on silica gel and eluted with benzene-acetone (9:1) to give 3-(3,4-dimethoxycinnamoylamino) -4-(2-methylphenyl)-7,8-dihydrocyclopenta[g] 1benzopyran-2(6H)-one as oil. The oil was crystallized from ethanol-isopropyl ether (648 mg, 67.4%). Recrystallization from acetone gave colorless needles, m.p. 159°-160° C.

Aufarbeitung

  1. distillationwas distilled off

Quellen und Nachweise

ORD-Eintrag
ord-03af43923d334bb58f46283316bba5de
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05418239

Verknüpfte Notizen

Wird geladen…