Sulfuric Acid → Acemetacin

HRID 745856

Reaktionsgleichung

[CH3:1][C:2]1[N:10]([C:11]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[O:12])[C:9]2[CH:8]=[CH:7][C:6]([O:20][CH3:21])=[CH:5][C:4]=2[C:3]=1[CH2:22][C:23]([OH:25])=[O:24].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:33][C:34]([O:36]C(C)(C)C)=[O:35].S(=O)(=O)(O)O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O.CC(C)=O>[CH3:1][C:2]1[N:10]([C:11]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[O:12])[C:9]2[CH:8]=[CH:7][C:6]([O:20][CH3:21])=[CH:5][C:4]=2[C:3]=1[CH2:22][C:23]([O:25][CH2:33][C:34]([OH:36])=[O:35])=[O:24]

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

25 g of indometacin, 10 g of potassium carbonate and 190 ml of acetone are stirred at 56° C. for 30 minutes. The mixture is cooled down to 40° C., 0.5 g of benzyltriethylammonium chloride is added, and 15.6 g of tert.-butyl chloroacetate are added dropwise. After 5 hours at 40° C. the reaction is complete (monitored by thin layer chromatography). The mixture is cooled down to 10° C. and 20 ml of concentrated sulphuric acid are then added dropwise in such a way that the temperature does not exceed 25° C. The mixture is stirred at 20° and 25° C. for 6 hours (monitored by thin layer chromatography), about 500 ml of water are added, and the solids are filtered off with suction, are dried in vacuo and are recrystallized from acetone-water.

Aufarbeitung

temperatureThe mixture is cooled down to 10° C.
customdoes not exceed 25° C
additionare added
filtrationthe solids are filtered off with suction
customare dried in vacuo
customare recrystallized from acetone-water

Quellen und Nachweise

ORD-Eintrag: ord-edaf7ff4775945c1a34edf8954dd028f
Quelldatensatz: uspto-grants-1986_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04600783

Verknüpfte Notizen

Wird geladen…