Hydrochloric Acid → 1-(p-Chlorobenzoyl)-2-methyl-5-methoxy-3-indolylacetic acid-ethoxymethyl ester

HRID 261451

Reaktionsgleichung

Reaktionsgleichung von HRID 261451
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([C:6]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[C:10]([CH2:19][C:20]([OH:22])=[O:21])=[C:9]2[CH3:23])=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:29][O:30][CH2:31][CH3:32].Cl>O1CCCC1>[CH2:31]([O:30][CH2:29][O:21][C:20](=[O:22])[CH2:19][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[N:8]([C:6](=[O:7])[C:5]2[CH:24]=[CH:25][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:9]=1[CH3:23])[CH3:32]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 3715IndomethacinHCID 18523Chloromethyl ethyl etherHCID 24758Sodium hydride

Produkt 1

HCID 203950521-(p-Chlorobenzoyl)-2-methyl-5-methoxy-3-indolylacetic acid-ethoxymethyl esterAusbeute 71,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 3.6 g of 1-(p-chlorobenzoyl)-2-methyl-5-methoxy-3-indolylacetic acid and 50 ml of dry tetrahydrofuran was added 0.5 g of 50% sodium hydride and the mixture was stirred for 30 minutes. To this mixture was further added 2.5 g of chloromethylethyl ether and the whole was reacted for 3 hours at room temperature. After the reaction was complete, the solvent was removed by distillation under reduced pressure. The residue thus obtained was neutralized with diluted hydrochloric acid, and then extracted with ethyl ether. The ether layer separated was washed with water and dried. The ether was removed by distillation to yield crystals. Recrystallization of the crystals from petroleum ether yielded 3.0 g of 1-(p-chlorobenzoyl)-2-methyl-5-methoxy-3-indolylacetic acid-ethoxymethyl ester as colorless prisms, melting at 60°-61° C. Analysis--Calculated for C22H22ClNO5 : C, 63.48; H, 5.17; N, 3.42. Found: C, 63.53; H, 5.33; N, 3.37.

Aufarbeitung

  1. customthe whole was reacted for 3 hours at room temperature
  2. customthe solvent was removed by distillation under reduced pressure
  3. customThe residue thus obtained
  4. extractionextracted with ethyl ether
  5. customThe ether layer separated
  6. washwas washed with water
  7. customdried
  8. customThe ether was removed by distillation
  9. customto yield crystals
  10. customRecrystallization of the crystals from petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-444d3cac27454ca8b8c1d3371b66890e
Quelldatensatz
uspto-grants-1979_08
Patentnummer
US04165428

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