Dimethylformamide → N-(4-(5-Cyano-1-ethyl-1H-pyrrol-2-yl)phenyl)ethanesulfonamide

HRID 1591839Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1591839
[C:1]([C:3]1[NH:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH2:18][CH3:19])(=[O:17])=[O:16])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)#[N:2].[CH3:20][C:21](C)([O-])C.[K+].C(I)C.CN(C)C=O>O1CCCC1>[C:1]([C:3]1[N:7]([CH2:20][CH3:21])[C:6]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][S:15]([CH2:18][CH3:19])(=[O:17])=[O:16])=[CH:12][CH:13]=2)=[CH:5][CH:4]=1)#[N:2]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 16051191N-[4-(5-Cyano-1H-pyrrol-2-yl)phenyl]ethanesulfonamideHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 16051192N-(4-(5-Cyano-1-ethyl-1H-pyrrol-2-yl)phenyl)ethanesulfonamideAusbeute 11 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N-[4-(5-cyano-1H-pyrrol-2-yl)phenyl]ethanesulfonamide (0.160 g, 0.58 mmol) was dissolved in tetrahydrofuran (10 mL). Potassium tert-butoxide (1.25 mL of a 1 M solution, 1.25 mmol) was dropwise added and the mixture stirred 15 minutes. Ethyl iodide (0.046 mL, 0.58 mmol) was dropwise added, followed by dimethyl formamide (5 mL) and the mixture stirred for 4 hours. The mixture was then partitioned between saturated ammonium chloride and ethyl acetate. The combined organic layers were dried over magnesium sulfate, and concentrated. The residue was purified by silica gel Flash Chromatography (hexane/ethyl acetate; 7:3) to afford the title compound (0.020 g, 11%).

Aufarbeitung

  1. stirringthe mixture stirred for 4 hours
  2. customThe mixture was then partitioned between saturated ammonium chloride and ethyl acetate
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel Flash Chromatography (hexane/ethyl acetate; 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-d52bfe79270f4b6bbb96a594325b8dc6
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07291643B2

Notizen zur Reaktion

Wird geladen…