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Triethylamine → HCID 18983825, Verbindung

HRID 1440469
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1440469
Br.[C:2]1([C:8]2[N:9]=[C:10]3[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][CH:13]=[CH:12][N:11]3[CH:21]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22]([N:24](CC)CC)C.ClS(N=C=O)(=O)=O>C(#N)C>[C:22]([C:21]1[N:11]2[CH:12]=[CH:13][CH:14]=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:10]2=[N:9][C:8]=1[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)#[N:24]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 67768891Ethyl 2-phenyl-imidazo[1,2-a]pyridine-8-carboxylate hydrogen bromide

Produkt 1

HCID 18983825HCID 18983825, VerbindungAusbeute 67,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

Ethyl 2-phenyl-imidazo[1,2-a]pyridine-8-carboxylate hydrogen bromide (1.96 g, 5.35 m mol), and triethylamine (0.55 g, 5.44 m mol) were added to acetonitrile (20 ml). To this solution was dropwise added a solution of chlorosulfonylisocyanate (ClSO2NCO) (0.8 ml, 9.19 m mol) in acetonitrile (5 ml) at an inner temperature of 0°-20° C. Then, the mixture was allowed to react at room temperature for an hour. After completion of the reaction, the mixture was concentrated under reduced pressure. The resulting concentrate to which water was added was extracted with dichloromethane, and the extract was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform) to give the object compound (1.06 g, yield 67.9%) as crystals. m.p. 87°-89° C.

Aufarbeitung

  1. customto react at room temperature for an hour
  2. customAfter completion of the reaction
  3. concentrationthe mixture was concentrated under reduced pressure
  4. concentrationThe resulting concentrate to which water
  5. additionwas added
  6. extractionwas extracted with dichloromethane
  7. washthe extract was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (eluent: chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-9149e09e3713462eaaa386625a1c5a6c
Quelldatensatz
uspto-grants-1996_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05498774

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