Indomethacin → Allyl 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-3-indoleacetoxyacetate

HRID 542583

Reaktionsgleichung

Reaktionsgleichung von HRID 542583
[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][CH2:37][CH:38]=[CH2:39])=[O:35]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.CC(C)=O>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([C:11]([N:10]2[C:9]3[C:4](=[CH:5][C:6]([O:20][CH3:21])=[CH:7][CH:8]=3)[C:3]([CH2:22][C:23]([O:25][CH2:33][C:34]([O:36][CH2:37][CH:38]=[CH2:39])=[O:35])=[O:24])=[C:2]2[CH3:1])=[O:12])=[CH:18][CH:17]=1

Komponenten

6

Edukt 3

HCID 3715IndomethacinHCID 11430Potassium CarbonateHCID 76206Allyl chloroacetate

Produkt 1

HCID 13654465Allyl 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-3-indoleacetoxyacetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 66133Benzyl triethylammonium chlorideKatalysatorHCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

25 g of indometacin, 10 g of potassium carbonate and 1.0 g of benzyltriethylammonium chloride in 140 ml of acetone are stirred for 30 minutes at 50° to 60° C. 10.1 g of allyl chloroacetate are then added dropwise over 5 minutes. The mixture is stirred at 40° C. until the reaction has ended (as checked by thin layer chromatography; about 3 hours). The mixture is filtered while warm, the filtrate is evaporated in vacuo and the residue is taken up in ether (about 90 ml) and mixed with petroleum ether (40 to 60) (about 30 ml). This mixture is left to stand over night at -10° C. and the product is then filtered off and dried in vacuo.

Aufarbeitung

  1. custom(as checked by thin layer chromatography; about 3 hours)
  2. filtrationThe mixture is filtered
  3. temperaturewhile warm
  4. customthe filtrate is evaporated in vacuo
  5. additionmixed with petroleum ether (40 to 60) (about 30 ml)
  6. waitThis mixture is left
  7. waitto stand over night at -10° C.
  8. filtrationthe product is then filtered off
  9. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3b0c8e80d6994da7b2c54c4961999ab1
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04658039

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