Water → Methyl 4-[(3-butyl-1-ethylthio-4-isoquinolinyl)-methyl]-benzoate

HRID 2260828

Reaktionsgleichung

Reaktionsgleichung von HRID 2260828
[CH2:1]([S:3][C:4]#[N:5])[CH3:2].O=[C:7]([CH2:26][CH2:27][CH2:28][CH3:29])[CH:8]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=1.O.[OH-].[NH4+]>P(Cl)(Cl)(Cl)=O>[CH2:26]([C:7]1[N:5]=[C:4]([S:3][CH2:1][CH3:2])[C:21]2[C:20]([C:8]=1[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:18][CH:19]=1)=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:27][CH2:28][CH3:29]

Komponenten

6

Edukt 4

HCID 962WaterHCID 10968Ethyl thiocyanateHCID 14923Ammonium HydroxideHCID 18999079Methyl 4-(3-oxo-2-phenyl-heptyl)-benzoate

Produkt 1

HCID 18999070Methyl 4-[(3-butyl-1-ethylthio-4-isoquinolinyl)-methyl]-benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24813Phosphorus oxychlorideLösungsmittel

Versuchsvorschrift

0.4 ml of ethyl thiocyanate and 0.45 ml of stannic chloride were added to a solution of 1 g of methyl 4-(3-oxo-2-phenyl-heptyl) benzoate of Step C in 20 ml of phosphorous oxychloride and the mixture was stirred for 10 hours at reflux, then poured into ice-cooled water. The mixture was stirred for 15 minutes and alkalized with concentrated ammonium hydroxide. Extraction was carried out with ethyl acetate and the extracts were washed with water, dried and evaporated to dryness. The residue was chromatographed on silica (eluant: hexane--ethyl acetate (9-1)) to obtain 0.57 g of the desired product melting at 70° C.

Aufarbeitung

  1. temperatureat reflux
  2. additionpoured into ice-
  3. stirringThe mixture was stirred for 15 minutes
  4. extractionExtraction
  5. washthe extracts were washed with water
  6. customdried
  7. customevaporated to dryness
  8. customThe residue was chromatographed on silica (eluant: hexane--ethyl acetate (9-1))

Quellen und Nachweise

ORD-Eintrag
ord-64c9eeabc9384717812dd60ee6024c17
Quelldatensatz
uspto-grants-1995_12
Patentnummer
US05478938

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