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Triethylamine → (E)-N,N-diallyl-4-(2-(4-bromophenyl)vinylsulfonamido)pyridine-3-sulfonamide

HRID 2283347
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2283347
C(N(CC)CC)C.[CH2:8]([N:11]([CH2:22][CH:23]=[CH2:24])[S:12]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:20]=1[NH2:21])(=[O:14])=[O:13])[CH:9]=[CH2:10].[Br:25][C:26]1[CH:31]=[CH:30][C:29](/[CH:32]=[CH:33]/[S:34](Cl)(=[O:36])=[O:35])=[CH:28][CH:27]=1>N1C=CC=CC=1>[CH2:22]([N:11]([CH2:8][CH:9]=[CH2:10])[S:12]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:20]=1[NH:21][S:34](/[CH:33]=[CH:32]/[C:29]1[CH:30]=[CH:31][C:26]([Br:25])=[CH:27][CH:28]=1)(=[O:35])=[O:36])(=[O:14])=[O:13])[CH:23]=[CH2:24]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 23084300(E)-2-(4-bromophenyl)ethene-1-sulfonyl chlorideHCID 57750998N,N-diallyl-4-aminopyridine-3-sulfonamide

Produkt 1

HCID 57751063(E)-N,N-diallyl-4-(2-(4-bromophenyl)vinylsulfonamido)pyridine-3-sulfonamideAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049
Pyridine
Lösungsmittel
2×

Versuchsvorschrift

Triethylamine (0.440 mL, 3.16 mmol) added was to a solution of N,N-diallyl-4-aminopyridine-3-sulfonamide (0.40 g, 1.58 mmol) in pyridine (10 mL), the mixture was stirred for 5 min and (E)-2-(4-bromophenyl)ethenesulfonyl chloride (0.53 g, 1.89 mmol) was added. After stirring over night the pyridine was evaporated, diluted hydrochloric acid was added and the mixture was extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and the solvent was evaporated. Purification by column chromatography, using chloroform/methanol (97:3) as the eluent, gave the title compound in 60% yield.

Aufarbeitung

  1. customwas evaporated
  2. additiondiluted hydrochloric acid was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. customthe solvent was evaporated
  6. customPurification by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1f907b8c63574329bb167839e0a88764
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09145380B2

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