N-(4-chloromethylphenyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide → N-(4-(benzylthiomethyl)phenyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide

HRID 565922Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 565922
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2[CH2:13][CH2:14][O:15][C:16]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=4)=[CH:19][C:17]=3[CH:18]=2)=[O:11])=[CH:5][CH:4]=1.[CH2:30]([S:37]CC1C=CC=CC=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[Na]>CN(C)C=O>[CH2:30]([S:37][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2[CH2:13][CH2:14][O:15][C:16]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=4)=[CH:19][C:17]=3[CH:18]=2)=[O:11])=[CH:5][CH:4]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Komponenten

4

Edukt 2

HCID 18472316N-(4-chloromethylphenyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamideHCID 69353784Sodium benzyl sulfide

Produkt 1

HCID 18472541N-(4-(benzylthiomethyl)phenyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamideAusbeute 149,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of N-(4-chloromethylphenyl)-7-(4-methyl-phenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (0.15g) and sodium benzyl sulfide (0.055g) in dimethylformamide (10ml) was stirred at room temperature over night. The solvent was evaporated, and to the residue was added water. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated to give crude crystals, which were recrystallized from ethyl acetate-hexane to give N-(4-(benzylthiomethyl)-phenyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (Compound 86) (0.17g) as colorless crystals.

Aufarbeitung

  1. customThe solvent was evaporated
  2. additionto the residue was added water
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated sodium chloride solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customUnder reduced pressure, the solvent was evaporated
  7. customto give crude crystals, which
  8. customwere recrystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-d6f58df7604c4242a9235ecc13a2c3c4
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06172061B2

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