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Hydrochloric Acid → N-benzyl-4-(1-benzylthio-1-methylethyl)-2-ethylidene-4-butanelactam

HRID 2211013
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2211013
Cl.Br[CH2:3]/[C:4](=[CH:9]\[CH3:10])/[C:5](OC)=[O:6].[CH2:11]([S:18][C:19]([CH3:30])([CH3:29])[CH:20]=[N:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl-].[NH4+]>C1COCC1.[Zn]>[CH2:22]([N:21]1[CH:20]([C:19]([S:18][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)([CH3:30])[CH3:29])[CH2:3][C:4](=[CH:9][CH3:10])[C:5]1=[O:6])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 11019705Methyl 2-bromomethylcrotonateHCID 19378136N-(2-benzylthio-2-methylpropylidene)benzylamine

Produkt 1

HCID 53674808N-benzyl-4-(1-benzylthio-1-methylethyl)-2-ethylidene-4-butanelactamAusbeute 19 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysator
HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

To a stirred suspension of zinc dust (0.53 g) activated with hydrochloric acid in THF (20 ml), methyl 2-bromomethylcrotonate (1.50 g) dissolved in THF (10 ml) and N-(2-benzylthio-2-methylpropylidene)benzylamine (2.00 g) dissolved in THF (10 ml) were added dropwise in the order named at about 30° C. under nitrogen atmosphere and ultrasonic irradiation. The mixture was stirred overnight at room temperature. To the mixture saturated aqueous ammonium chloride solution was added. The mixture was filtered by celite. A reaction product was extracted with ethyl acetate from the filtrate. The organic layer was washed with IN hydrochloric acid, water and then saturated sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The oily residue was purified by silica gel column chromatography to give 1.03 g (40%) of the titled compound No.7-1 and 0.48 g (19%) of the titled compound No.7-2.

Aufarbeitung

  1. additionwere added dropwise in the order
  2. customnamed at about 30° C. under nitrogen atmosphere
  3. customultrasonic irradiation
  4. filtrationThe mixture was filtered by celite
  5. extractionA reaction product was extracted with ethyl acetate from the filtrate
  6. washThe organic layer was washed with IN hydrochloric acid, water
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe oily residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e03ea93b583047caa0a9dd1057e4706b
Quelldatensatz
uspto-grants-1995_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05461158

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