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Hydrochloric Acid → 4'-[15-(Trifluoromethyl)pentadecylamino]-2-(phenylsulfonyl)acetophenone

HRID 1105915
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1105915
[H-].[Na+].[CH3:3][S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:6])=[O:5].[F:13][C:14]([F:42])([F:41])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][NH:30][C:31]1[CH:40]=[CH:39][C:34]([C:35](OC)=[O:36])=[CH:33][CH:32]=1.Cl>O1CCCC1.COCCOC>[F:13][C:14]([F:41])([F:42])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][NH:30][C:31]1[CH:40]=[CH:39][C:34]([C:35](=[O:36])[CH2:3][S:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)(=[O:6])=[O:5])=[CH:33][CH:32]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 18369Methyl phenyl sulfoneHCID 24758Sodium hydrideHCID 20549341Methyl 4-[15-(trifluoromethyl)pentadecylamino]benzoate

Produkt 1

HCID 205493644'-[15-(Trifluoromethyl)pentadecylamino]-2-(phenylsulfonyl)acetophenone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028
Tetrahydrofuran
Lösungsmittel
HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A solution of 864 mg. of sodium hydride and 5.3 g. of methylphenylsulfone in 20 ml. of 1,2-dimethoxyethane is stirred at 60° C. for one hour under an atmosphere of argon. To this solution is then added a solution of 5.0 g. of methyl 4-[15-(trifluoromethyl)pentadecylamino]benzoate and 50 ml. of tetrahydrofuran and the reaction mixture is stirred at 60° C. for 1.5 hours. The mixture is cooled, poured onto ice, acidified with dilute hydrochloric acid to pH 3 and then extracted with chloroform. The organic layer is separated, washed three times with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated to dryness. The crude solid is chromatographed on silica gel, eluting with methylene chloride to yield the product.

Aufarbeitung

  1. additionTo this solution is then added a solution of 5.0 g
  2. temperatureThe mixture is cooled
  3. additionpoured onto ice
  4. extractionextracted with chloroform
  5. customThe organic layer is separated
  6. washwashed three times with water and saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated to dryness
  9. customThe crude solid is chromatographed on silica gel
  10. washeluting with methylene chloride
  11. customto yield the product

Quellen und Nachweise

ORD-Eintrag
ord-eabf4c3e91624879893656e3b948cbcf
Quelldatensatz
uspto-grants-1982_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04310545

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