Potassium Carbonate → HCID 68451991, Verbindung

HRID 2355067Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2355067
Cl.[Br:2][C:3]1[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=1[O:5][CH:6]1[CH2:10][NH:9][CH2:8][CH2:7]1.Br[C:16]1[S:20][C:19]([C:21]#[N:22])=[N:18][N:17]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:2][C:3]1[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=1[O:5][C@H:6]1[CH2:7][CH2:8][N:9]([C:16]2[S:20][C:19]([C:21]#[N:22])=[N:18][N:17]=2)[CH2:10]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 533885265-Bromo-1,3,4-thiadiazole-2-carbonitrileHCID 53409201HCID 53409201, Verbindung

Produkt 1

HCID 68451991HCID 68451991, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a mixture of 4-(2-bromophenoxy)pyrrolidine hydrochloride (0.5 g, 1.87 mmol) and 5-bromo-1,3,4-thiadiazole-2-carbonitrile (0.36 g, 1.87 mmol) in DMF (10 mL) was added K2CO3 (0.77 g, 5.61 mmol) under a nitrogen atmosphere. The mixture was stirred at 70° C. for 4 h. After dilution with water, the mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered and purified by preparative TLC with petroleum:EtOAc (2:1) to give the title compound. 1H NMR (300 MHz, CDCl3): δ 7.58 (d, 1H), 7.52 (t, 1H), 7.08 (t, 1H), 6.99 (d, 1H), 5.24 (m, 1H), 3.69-3.93 (m, 4H), 2.33-2.56 (m, 2H).

Aufarbeitung

  1. extractionAfter dilution with water, the mixture was extracted with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. custompurified by preparative TLC with petroleum:EtOAc (2:1)

Quellen und Nachweise

ORD-Eintrag
ord-672b6f16f4414f8c9913d70350e21785
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07754745B2

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