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

HRID 258031

Reaktionsgleichung

Reaktionsgleichung von HRID 258031
[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 (MgSO<) and distilled to remove the solvent. The residue was chromatographed on silica gel and eluted with benzeneacetone (9:1) to give 3-(3,4-dimethoxycinnamoylamino)-4-(2-methylphenyl)-7,8-dihydrocyclopenta[g][1]benzopyran-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-eaef6ab8e70d49268db2f8e05d0ad830
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05264454

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