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Pyridine → HCID 135927746, Verbindung

HRID 2241171
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2241171
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:31][CH3:32])=[C:6]([S:8]([NH:11][C:12]2[CH:13]=[C:14]([CH:28]=[CH:29][CH:30]=2)[C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([C:24](=[NH:27])[NH:25][OH:26])=[CH:20][CH:19]=2)=[O:16])(=[O:10])=[O:9])[CH:7]=1.N1C=CC=CC=1.C(C(CCCC)[CH2:42][O:43]C(Cl)=O)C>CN(C)C=O.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:31][CH3:32])=[C:6]([S:8]([NH:11][C:12]2[CH:13]=[C:14]([CH:28]=[CH:29][CH:30]=2)[C:15]([NH:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]3[NH:27][C:42](=[O:43])[O:26][N:25]=3)=[CH:22][CH:23]=2)=[O:16])(=[O:10])=[O:9])[CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 627832-Ethylhexyl chloroformateHCID 1784907253-(5-chloro-2-methoxy-benzenesulfonylamino)-N-[4-(N-hydroxycarbamimidoyl)-phenyl]-benzamide

Produkt 1

HCID 135927746HCID 135927746, VerbindungAusbeute 76,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 3-(5-chloro-2-methoxy-benzenesulfonylamino)-N-[4-(N-hydroxycarbamimidoyl)-phenyl]-benzamide (145 mg, 0.30 mmol) in dimethylformamide (2.0 ml) was treated with pyridine (26 mg, 1.08 equiv.) and cooled to 0° C. Chloroformic acid 2-ethylhexyl ester (59 mg, 0.30 mmol, 1 equiv.) in DMF (0.1 ml) was added dropwise. The mixture was stirred at 0° C. for 30 min, then diluted with water and extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and evaporated. The residue was suspended in xylene and the mixture was stirred at 100° C. for 1 h and then at 145° C. for 1 h. After cooling to room temperature, the precipitated solid was filtered, washing with xylene, and dried under high vacuum to yield the title compound (115 mg, 75%) as a white solid, MS (ISP): m/e=499.0 (M−H).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. customevaporated
  4. stirringthe mixture was stirred at 100° C. for 1 h
  5. waitat 145° C. for 1 h
  6. temperatureAfter cooling to room temperature
  7. filtrationthe precipitated solid was filtered
  8. washwashing with xylene
  9. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-fae37e0334634b4094a9bc05c76e99a2
Quelldatensatz
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07723538B2

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