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Pyridine → (2-Butyl-5-methylsulfanylamino-benzofuran-3-yl)-[4-(3-dibutylamino-propoxy)-phenyl]-methanone

HRID 1771253
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1771253
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][CH2:11][CH2:12][CH3:13])=[C:7]([C:14]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][N:26]([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH2:29][CH3:30])=[CH:18][CH:17]=3)=[O:15])[C:6]=2[CH:35]=1.N1C=CC=CC=1.[CH3:42][S:43]Cl>O>[CH2:10]([C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([NH:1][S:43][CH3:42])=[CH:35][C:6]=2[C:7]=1[C:14]([C:16]1[CH:17]=[CH:18][C:19]([O:22][CH2:23][CH2:24][CH2:25][N:26]([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:31][CH2:32][CH2:33][CH3:34])=[CH:20][CH:21]=1)=[O:15])[CH2:11][CH2:12][CH3:13]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 138595MethanesulfenylchlorideHCID 11488441(5-Amino-2-butylbenzofuran-3-yl)(4-(3-(dibutylamino)propoxy)phenyl)methanone

Produkt 1

HCID 71711318(2-Butyl-5-methylsulfanylamino-benzofuran-3-yl)-[4-(3-dibutylamino-propoxy)-phenyl]-methanoneAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

4.78 g of (5-amino-2-butyl-benzofuran-3-yl)-[4-(3-dibutylamino-propoxy)-phenyl]-methanone (III) (0.01 mol, 1 eq) and 35 mL of pyridine were placed into a flask. The mixture was cooled down to 0° C. and 0.99 g of methanesulfenyl chloride (II) (0.012 mol, 1.2 eq; freshly prepared as described in the above mentioned literature) was added in 10 min. The mixture was stirred at 0° C. for 3 hours and then heated to room temperature and stirred for 6 hours. The mixture was poured into 100 mL of water. The product was extracted with 50 mL of dichloromethane. The organic phase was washed with 30 mL of water. The solvent was evaporated and the product was purified by column chromatography (column: spheric silica (60 Å); eluent: toluene:ethyl acetate=70:30) to obtain 2.2 g of compound (IV) (42%) as a light yellow oil.

Aufarbeitung

  1. customfreshly prepared
  2. additionwas added in 10 min
  3. temperatureheated to room temperature
  4. stirringstirred for 6 hours
  5. extractionThe product was extracted with 50 mL of dichloromethane
  6. washThe organic phase was washed with 30 mL of water
  7. customThe solvent was evaporated
  8. customthe product was purified by column chromatography (column: spheric silica (60 Å); eluent: toluene:ethyl acetate=70:30)

Quellen und Nachweise

ORD-Eintrag
ord-c4fb2175e4de4421b23f3a162ca82f8c
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09249119B2

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