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Thiomorpholine → 7-(4-methylphenyl)-N-[4-(thiomorpholinomethyl)phenyl]-3,4-dihydronaphthalene-2-carboxamide

HRID 565895
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 565895
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][C:16]([C:22]4[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=4)=[CH:17][CH:18]=3)[CH:13]=2)=[O:11])=[CH:5][CH:4]=1.[NH:29]1[CH2:34][CH2:33][S:32][CH2:31][CH2:30]1.C(=O)([O-])O.[Na+]>C1COCC1>[CH3:28][C:25]1[CH:24]=[CH:23][C:22]([C:16]2[CH:15]=[C:14]3[C:19]([CH2:20][CH2:21][C:12]([C:10]([NH:9][C:6]4[CH:5]=[CH:4][C:3]([CH2:2][N:29]5[CH2:34][CH2:33][S:32][CH2:31][CH2:30]5)=[CH:8][CH:7]=4)=[O:11])=[CH:13]3)=[CH:18][CH:17]=2)=[CH:27][CH:26]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 67164ThiomorpholineHCID 516892Sodium BicarbonateHCID 18472361N-[4-(chloromethyl)phenyl]-7-(4-methylphenyl)-3,4-dihydronaphthalene-2-carboxamide

Produkt 1

HCID 184725127-(4-methylphenyl)-N-[4-(thiomorpholinomethyl)phenyl]-3,4-dihydronaphthalene-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

In THF (10ml) was dissolved N-[4-(chloromethyl)-phenyl]-7-(4-methylphenyl)-3,4-dihydro-naphthalene-2-carboxamide (300mg), and to the mixture was added thiomorpholine (233 μl). The mixture was refluxed for 20 hours. The reaction mixture was cooled to room temperature, and to the mixture was added 5% sodium hydrogen carbonate solution (50ml). The mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give 7-(4methylphenyl)-N-[4-(thiomorpholinomethyl)-phenyl]-3,4-dihydro-naphthalene-2-carboxamide (Compound 50) (309mg) as colorless crystals.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 20 hours
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium chloride solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-0ca652365a884a2c82c06439d00e8dcb
Quelldatensatz
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06172061B2

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