Sodium Carbonate → 3,4-dihydrobenzothieno[2,3-c]-pyridine-2(1H)-butanenitrile

HRID 2298879

Reaktionsgleichung

Reaktionsgleichung von HRID 2298879
[CH2:1]1[C:6]2[S:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:5]=2[CH2:4][CH2:3][NH:2]1.C([O-])([O-])=O.[Na+].[Na+].Cl[CH2:21][CH2:22][CH2:23][C:24]#[N:25]>C(#N)C.CC1C=CC=CC=1>[CH2:1]1[C:6]2[S:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:5]=2[CH2:4][CH2:3][N:2]1[CH2:21][CH2:22][CH2:23][C:24]#[N:25]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 123364-ChlorobutyronitrileHCID 4132821,2,3,4-Tetrahydro[1]benzothieno[2,3-c]pyridine

Produkt 1

HCID 183789583,4-dihydrobenzothieno[2,3-c]-pyridine-2(1H)-butanenitrileAusbeute 101,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 1,2,3,4-tetrahydro-[1]benzothieno[2,3-c]pyridine (0.02 mol), Na2CO3 (5 g), KI (0.1 g) and 4-chlorobutanenitrile (0.025 mol) in acetonitrile (50 ml) and methylbenzene (150 ml) was stirred and refluxed overnight, then cooled, filtered and the filtrate was evaporated. The residue (oil) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2). The pure fractions were collected and the solvent was evaporated, yielding 5.2 g of 3,4-dihydrobenzothieno[2,3-c]-pyridine-2(1H)-butanenitrile (interm. 6).

Aufarbeitung

  1. temperaturerefluxed overnight
  2. temperaturecooled
  3. filtrationfiltered
  4. customthe filtrate was evaporated
  5. customThe residue (oil) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2)
  6. customThe pure fractions were collected
  7. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-fde6fc8e3ab44b2f98e46e198b471392
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06495555B1

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